Triethylamine → HCID 59324066, compound

HRID 2063690Notes

Reaction equation

HRID 2063690 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:15][C:16]2[S:17][CH:18]=[C:19]([C:21](O)=[O:22])[N:20]=2)[CH:6]=[CH:7][C:8]=1[N:9]1[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10]1.Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C.[F:54][C:55]1[CH:62]=[CH:61][C:58]([CH2:59][NH2:60])=[CH:57][CH:56]=1>ClCCl>[F:54][C:55]1[CH:62]=[CH:61][C:58]([CH2:59][NH:60][C:21]([C:19]2[N:20]=[C:16]([NH:15][C:5]3[CH:6]=[CH:7][C:8]([N:9]4[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10]4)=[C:3]([O:2][CH3:1])[CH:4]=3)[S:17][CH:18]=2)=[O:22])=[CH:57][CH:56]=1

Participants

7

Reactant 5

HCID 8471Triethylamine2×HCID 673264-Fluorobenzylamine2×HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride2×HCID 27960291-Hydroxybenzotriazole hydrate2×HCID 86641714HCID 86641714, compound

Product 1

HCID 59324066HCID 59324066, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a suspension of 2-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenylamino]-thiazole-4-carboxylic acid (61.5 mg, purity 43%, 0.080 mmol) in dichloromethane (2 ml) were added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (24.5 mg, 0.128 mmol), 1-hydroxybenzotriazole hydrate (19.6 mg, 0.128 mmol), triethylamine (30.0 mg, 0.296 mmol) and a solution of 4-fluorobenzyl amine (12 mg, 0.096 mmol) in dichloromethane (1 ml). After 12 h at rt again 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (24.5 mg, 0.128 mmol), 1-hydroxybenzotriazole hydrate (19.6 mg, 0.128 mmol), triethylamine (30.0 mg, 0.296 mmol) and a solution of 4-fluorobenzyl amine (12 mg, 0.096 mmol) in dichloromethane (1 ml) were added. After 12 h at rt the reaction mixture was directly purified by silica gel chromatography using dichloromethane/methanol as eluent. The title compound was obtained as a off-white foam (23.0 mg, 66%). MS ISP (m/e): 438.2 (14) [(M+H)+].

Workup

  1. customAfter 12 h at rt the reaction mixture was directly purified by silica gel chromatography

Sources & evidence

ORD record
ord-44bd9dd6d8a24df7a473c92c532c38fc
Source dataset
uspto-grants-2012_10
Patent number
US08288403B2

Reaction notes

Loading…