1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 118451572, compound

HRID 522842Notes

Reaction equation

HRID 522842 reaction equation
[CH2:1]([O:8][C:9]([N:11](C(OCC1C=CC=CC=1)=O)[C:12]1[C:21]2[N:22]=[C:23]([CH2:30][O:31][CH2:32][CH3:33])[N:24]([CH2:25][C:26]([OH:29])([CH3:28])[CH3:27])[C:20]=2[C:19]2[CH:18]=[CH:17][C:16]([CH2:34][CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])=[CH:15][C:14]=2[N:13]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:51]([N:58]([CH2:63][C:64]1[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=1)[CH2:59][C:60](O)=[O:61])[C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1.C(N=C=NCCCN(C)C)C>CN(C1C=CN=CC=1)C.ClCCl>[CH2:1]([O:8][C:9]([NH:11][C:12]1[C:21]2[N:22]=[C:23]([CH2:30][O:31][CH2:32][CH3:33])[N:24]([CH2:25][C:26]([O:29][C:60](=[O:61])[CH2:59][N:58]([CH2:51][C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=3)[CH2:63][C:64]3[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=3)([CH3:28])[CH3:27])[C:20]=2[C:19]2[CH:18]=[CH:17][C:16]([CH2:34][CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])=[CH:15][C:14]=2[N:13]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 1740822-(Dibenzylamino)acetic acidHCID 118451586HCID 118451586, compound

Product 1

HCID 118451572HCID 118451572, compoundYield 52.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of ethyl 3-(4-(bis(benzyloxycarbonyl)amino)-2-(ethoxymethyl)-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-7-yl)propanoate (300 mg, 439 μmol), 2-(dibenzylamino)acetic acid (337 mg, 1.32 mmol) and DMAP (107 mg, 879 μmol) in dichloromethane (4 mL) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (253 mg, 1.32 mmol) and molecular sieves (300 mg). After 1 h stirring at room temperature starting materials had dissolved, stirring at room temperature continued for 6 h and the mixture was left standing over the weekend. The residue was diluted with dichloromethane (50 mL) and washed with HCl (1 M, 20 mL) and water (20 mL). The aqueous phase was extracted with dichloromethane (50 mL), organic phases were combined, dried with MgSO4 and concentrated in vacuo. The residue was purified by flash chromatography (silica gel, 0% to 100% ethyl acetate in heptane) to give the title compound (182 mg, 52%) as light yellow oil; LC-MS (UV peak area, ESI) 98%, 784.6 (MH+).

Workup

  1. dissolutionhad dissolved
  2. stirringstirring at room temperature
  3. waitcontinued for 6 h
  4. waitthe mixture was left
  5. washwashed with HCl (1 M, 20 mL) and water (20 mL)
  6. extractionThe aqueous phase was extracted with dichloromethane (50 mL), organic phases
  7. dry with materialdried with MgSO4
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by flash chromatography (silica gel, 0% to 100% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-f22f1e3c257d4a1693bafa3e4f052eab
Source dataset
uspto-grants-2016_05
Patent number
US09334268B2

Reaction notes

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