1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 117703055, compound

HRID 531425Notes

Reaction equation

HRID 531425 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[C:11](=[O:133])[O:12][C:13]2[C:18]([CH:19]=1)=[CH:17][CH:16]=[C:15]([N:20]([CH2:24][C:25]1[N:26]=[N:27][N:28]([CH2:30][O:31][CH2:32][CH2:33][O:34][CH2:35][CH2:36][O:37][C:38]3[CH:39]=[C:40]([CH:54]=[C:55]([O:95][CH2:96][CH2:97][O:98][CH2:99][CH2:100][O:101][CH2:102][N:103]4[CH:107]=[C:106]([CH2:108][N:109]([C:113]5[CH:122]=[C:121]6[C:116]([CH:117]=[C:118]([C:124]7[S:125][C:126]8[CH:132]=[CH:131][CH:130]=[CH:129][C:127]=8[N:128]=7)[C:119](=[O:123])[O:120]6)=[CH:115][CH:114]=5)[CH:110]([CH3:112])[CH3:111])[N:105]=[N:104]4)[C:56]=3[O:57][CH2:58][CH2:59][O:60][CH2:61][CH2:62][O:63][CH2:64][N:65]3[CH:69]=[C:68]([CH2:70][N:71]([C:75]4[CH:84]=[C:83]5[C:78]([CH:79]=[C:80]([C:86]6[S:87][C:88]7[CH:94]=[CH:93][CH:92]=[CH:91][C:89]=7[N:90]=6)[C:81](=[O:85])[O:82]5)=[CH:77][CH:76]=4)[CH:72]([CH3:74])[CH3:73])[N:67]=[N:66]3)[C:41]([NH:43][CH2:44][C:45]3[CH:53]=[CH:52][C:48]([C:49]([OH:51])=[O:50])=[CH:47][CH:46]=3)=[O:42])[CH:29]=1)[CH:21]([CH3:23])[CH3:22])[CH:14]=2.O[N:135]1[C:139](=[O:140])[CH2:138][CH2:137][C:136]1=[O:141].CCN=C=NCCCN(C)C>C(Cl)Cl>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[C:11](=[O:133])[O:12][C:13]2[C:18]([CH:19]=1)=[CH:17][CH:16]=[C:15]([N:20]([CH2:24][C:25]1[N:26]=[N:27][N:28]([CH2:30][O:31][CH2:32][CH2:33][O:34][CH2:35][CH2:36][O:37][C:38]3[CH:39]=[C:40]([CH:54]=[C:55]([O:95][CH2:96][CH2:97][O:98][CH2:99][CH2:100][O:101][CH2:102][N:103]4[CH:107]=[C:106]([CH2:108][N:109]([C:113]5[CH:122]=[C:121]6[C:116]([CH:117]=[C:118]([C:124]7[S:125][C:126]8[CH:132]=[CH:131][CH:130]=[CH:129][C:127]=8[N:128]=7)[C:119](=[O:123])[O:120]6)=[CH:115][CH:114]=5)[CH:110]([CH3:112])[CH3:111])[N:105]=[N:104]4)[C:56]=3[O:57][CH2:58][CH2:59][O:60][CH2:61][CH2:62][O:63][CH2:64][N:65]3[CH:69]=[C:68]([CH2:70][N:71]([C:75]4[CH:84]=[C:83]5[C:78]([CH:79]=[C:80]([C:86]6[S:87][C:88]7[CH:94]=[CH:93][CH:92]=[CH:91][C:89]=7[N:90]=6)[C:81](=[O:85])[O:82]5)=[CH:77][CH:76]=4)[CH:72]([CH3:74])[CH3:73])[N:67]=[N:66]3)[C:41]([NH:43][CH2:44][C:45]3[CH:46]=[CH:47][C:48]([C:49]([O:51][N:135]4[C:139](=[O:140])[CH2:138][CH2:137][C:136]4=[O:141])=[O:50])=[CH:52][CH:53]=3)=[O:42])[CH:29]=1)[CH:21]([CH3:23])[CH3:22])[CH:14]=2

Participants

5

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 80170N-HydroxysuccinimideHCID 117703136HCID 117703136, compound

Product 1

HCID 117703055HCID 117703055, compoundYield 92.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution in which the 4-((3,4,5-tris(2-(2-((4-(((3-(benzo[d]thiazol-2-yl)-2-oxo-2H-chromen-7-yl)(isopropyl)amino)methyl)-1H-1,2,3-triazol-1-yl)methoxy)ethoxy) ethoxy)benzamido)methyl)benzoic acid (100 mg, 0.053 mmol) compound of Chemical Formula 17 was dissolved in methylene chloride (2 mL), N-hydroxy succinimide (243.9 mg, 2.12 mmol) and EDAC (406.4 mg, 2.12 mmol) were added in order at 0° C., and the mixture was stirred overnight at room temperature. After the post-reaction mixture was partitioned to methylene chloride (20 mL) and distilled water (20 mL), the separated organic layer was washed with saturated salted water (10 mL), dried with anhydrous sodium sulfate, then filtered, and the resulting filtrate was vacuum distilled. The residue obtained was column chromatographed on silica gel (chloroform/methanol (20:1)) to give 2,5-dioxopyrrolidin-1-yl 4-((3,4,5-tris(2-(2-((4-(((3-(benzo[d]thiazol-2-yl)-2-oxo-2H-chromen-7-yl)(isopropyl)amino)methyl)-1H-1,2,3-triazol-1-yl)methoxy)ethoxy)ethoxy)benz amido)methyl)benzoate (96 mg, 92%). 1H NMR (500 MHz, CDCl3) δ 10.04 (s, 3H), 8.32 (d, 2H, J=8.2 Hz), 8.11 (d, 3H, J=9.6 Hz), 7.93 (d, 4H, J=7.3 Hz), 7.74 (d, 3H, J=7.3 Hz), 7.45-7.60 (m, 9H), 7.37 (m, 3H), 6.82 (m, 3H), 6.65 (s, 3H), 4.53-4.70 (m, 14H), 4.34 (m, 3H), 4.01-4.13 (m, 6H), 3.82 (m, 9H), 3.65 (m, 6H), 3.52 (m, 12H), 2.91 (s, 4H), 1.25 (d, 18H, J=6.4 Hz).

Workup

  1. customAfter the post-reaction mixture was partitioned to methylene chloride (20 mL)
  2. distillationdistilled water (20 mL)
  3. washthe separated organic layer was washed with saturated salted water (10 mL)
  4. dry with materialdried with anhydrous sodium sulfate
  5. filtrationfiltered
  6. distillationdistilled
  7. customThe residue obtained
  8. customchromatographed on silica gel (chloroform/methanol (20:1))

Sources & evidence

ORD record
ord-e8a0a27fe4f145d2a3adeaf676f16baf
Source dataset
uspto-grants-2016_05
Patent number
US09354234B2

Reaction notes

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