Ethanol → HCID 117703136, compound

HRID 531424Notes

Reaction equation

HRID 531424 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:142])[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:63]=[C:64]([O:104][CH2:105][CH2:106][O:107][CH2:108][CH2:109][O:110][CH2:111][N:112]4[CH:116]=[C:115]([CH2:117][N:118]([C:122]5[CH:131]=[C:130]6[C:125]([CH:126]=[C:127]([C:133]7[S:134][C:135]8[CH:141]=[CH:140][CH:139]=[CH:138][C:136]=8[N:137]=7)[C:128](=[O:132])[O:129]6)=[CH:124][CH:123]=5)[CH:119]([CH3:121])[CH3:120])[N:114]=[N:113]4)[C:65]=3[O:66][CH2:67][CH2:68][O:69][CH2:70][CH2:71][O:72][CH2:73][N:74]3[CH:78]=[C:77]([CH2:79][N:80]([C:84]4[CH:93]=[C:92]5[C:87]([CH:88]=[C:89]([C:95]6[S:96][C:97]7[CH:103]=[CH:102][CH:101]=[CH:100][C:98]=7[N:99]=6)[C:90](=[O:94])[O:91]5)=[CH:86][CH:85]=4)[CH:81]([CH3:83])[CH3:82])[N:76]=[N:75]3)[C:41]([NH:43][CH2:44][C:45]3[CH:62]=[CH:61][C:48]([C:49]([O:51]CC4C=CC(OC)=CC=4)=[O:50])=[CH:47][CH:46]=3)=[O:42])[CH:29]=1)[CH:21]([CH3:23])[CH3:22])[CH:14]=2.FC(F)(F)C(O)=O.C(O)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:142])[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:63]=[C:64]([O:104][CH2:105][CH2:106][O:107][CH2:108][CH2:109][O:110][CH2:111][N:112]4[CH:116]=[C:115]([CH2:117][N:118]([C:122]5[CH:131]=[C:130]6[C:125]([CH:126]=[C:127]([C:133]7[S:134][C:135]8[CH:141]=[CH:140][CH:139]=[CH:138][C:136]=8[N:137]=7)[C:128](=[O:132])[O:129]6)=[CH:124][CH:123]=5)[CH:119]([CH3:121])[CH3:120])[N:114]=[N:113]4)[C:65]=3[O:66][CH2:67][CH2:68][O:69][CH2:70][CH2:71][O:72][CH2:73][N:74]3[CH:78]=[C:77]([CH2:79][N:80]([C:84]4[CH:93]=[C:92]5[C:87]([CH:88]=[C:89]([C:95]6[S:96][C:97]7[CH:103]=[CH:102][CH:101]=[CH:100][C:98]=7[N:99]=6)[C:90](=[O:94])[O:91]5)=[CH:86][CH:85]=4)[CH:81]([CH3:83])[CH3:82])[N:76]=[N:75]3)[C:41]([NH:43][CH2:44][C:45]3[CH:46]=[CH:47][C:48]([C:49]([OH:51])=[O:50])=[CH:61][CH:62]=3)=[O:42])[CH:29]=1)[CH:21]([CH3:23])[CH3:22])[CH:14]=2

Participants

5

Reactant 3

HCID 702EthanolHCID 6422Trifluoroacetic acidHCID 117702870HCID 117702870, compound

Product 1

HCID 117703136HCID 117703136, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution in which the 4-methoxybenzyl 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)benzoate (120 mg, 0.06 mmol) compound of Chemical Formula 16 was dissolved in methylene chloride (2 mL), trifluoroacetic acid (1 mL) was added at room temperature, and the mixture was stirred for 36 hours at the same temperature. Ethanol (10 mL) was added together when the post-reaction mixture was vacuum distilled to remove trifluoroacetic acid. This vacuum distillation was repeated 6 times to give 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 (105.7 mg, 95%), and the product was immediately used for the next reaction without further purification.

Workup

  1. distillationdistilled
  2. customto remove trifluoroacetic acid
  3. distillationThis vacuum distillation

Sources & evidence

ORD record
ord-aeb770fc863a4deb93125e31b10d7dd7
Source dataset
uspto-grants-2016_05
Patent number
US09354234B2

Reaction notes

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