Triethylamine → Ethyl 3-(5-(5-chloro-2-((4'-chloro-2'-methyl-[1,1'-biphenyl]-4-yl)carbamoyl)phenyl)picolinamido)propanoate

HRID 405229Notes

Reaction equation

HRID 405229 reaction equation
[CH3:1][CH2:2]N(CC)CC.[C:8]([CH2:11][CH2:12][NH:13][C:14]([C:16]1[N:21]=[CH:20][C:19]([C:22]2[CH:30]=[C:29]([Cl:31])[CH:28]=[CH:27][C:23]=2[C:24]([OH:26])=O)=[CH:18][CH:17]=1)=[O:15])([OH:10])=[O:9].[Cl:32][C:33]1[CH:38]=[CH:37][C:36]([C:39]2[CH:44]=[CH:43][C:42]([NH2:45])=[CH:41][CH:40]=2)=[C:35]([CH3:46])[CH:34]=1.CCN=C=NCCCN(C)C>C(Cl)Cl>[Cl:31][C:29]1[CH:28]=[CH:27][C:23]([C:24](=[O:26])[NH:45][C:42]2[CH:43]=[CH:44][C:39]([C:36]3[CH:37]=[CH:38][C:33]([Cl:32])=[CH:34][C:35]=3[CH3:46])=[CH:40][CH:41]=2)=[C:22]([C:19]2[CH:18]=[CH:17][C:16]([C:14]([NH:13][CH2:12][CH2:11][C:8]([O:10][CH2:1][CH3:2])=[O:9])=[O:15])=[N:21][CH:20]=2)[CH:30]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 672116234'-Chloro-2'-methyl-[1,1'-biphenyl]-4-amineHCID 710599982-(6-((2-Carboxyethyl)carbamoyl)pyridin-3-yl)-4-chlorobenzoic acid

Product 1

HCID 71059976Ethyl 3-(5-(5-chloro-2-((4'-chloro-2'-methyl-[1,1'-biphenyl]-4-yl)carbamoyl)phenyl)picolinamido)propanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Neat Et3N (0.14 mL, 1.0 mmol) was added to a DCM mixture (5 mL) of 2-(6-((2-carboxyethyl)carbamoyl)pyridin-3-yl)-4-chlorobenzoic acid (226 mg, 0.6 mmol), 4′-chloro-2′-methyl-[1,1′-biphenyl]-4-amine (109 mg, 0.5 mmol), and EDCI (192 mg, 1.0 mmol) and the resulting mixture was stirred at room temperature. After 3 h the resulting mixture was directly purified via column chromatography to yield the title compound.

Workup

  1. customAfter 3 h the resulting mixture was directly purified via column chromatography

Sources & evidence

ORD record
ord-08dd0fdb954b40fc977ac252d60e7cfb
Source dataset
uspto-grants-2014_06
Patent number
US08748624B2

Reaction notes

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