Triethylamine → 4-(cyclopropoxy)-N-[1-(5,6-dihydro-4H-imidazo[1,2-a][1]benzazepin-4-ylcarbamoyl)cyclopropyl]benzamide

HRID 2068553Notes

Reaction equation

HRID 2068553 reaction equation
[CH:1]1[N:5]2[C:6]3[CH:15]=[CH:14][CH:13]=[CH:12][C:7]=3[CH2:8][CH2:9][CH:10]([NH2:11])[C:4]2=[N:3][CH:2]=1.[CH:16]1([O:19][C:20]2[CH:34]=[CH:33][C:23]([C:24]([NH:26][C:27]3([C:30](O)=[O:31])[CH2:29][CH2:28]3)=[O:25])=[CH:22][CH:21]=2)[CH2:18][CH2:17]1.Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C>ClCCl>[CH:16]1([O:19][C:20]2[CH:21]=[CH:22][C:23]([C:24]([NH:26][C:27]3([C:30](=[O:31])[NH:11][CH:10]4[CH2:9][CH2:8][C:7]5[CH:12]=[CH:13][CH:14]=[CH:15][C:6]=5[N:5]5[CH:1]=[CH:2][N:3]=[C:4]45)[CH2:29][CH2:28]3)=[O:25])=[CH:33][CH:34]=2)[CH2:18][CH2:17]1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 583040445,6-dihydro-4H-imidazo[1,2-a][1]benzazepin-4-amineHCID 672344531-(4-Cyclopropoxybenzamido)cyclopropanecarboxylic acid

Product 1

HCID 672348194-(cyclopropoxy)-N-[1-(5,6-dihydro-4H-imidazo[1,2-a][1]benzazepin-4-ylcarbamoyl)cyclopropyl]benzamideYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 5,6-dihydro-4H-imidazo[1,2-a][1]benzazepin-4-amine (400 mg, 2.01 mmol), 1-(4-cyclopropoxybenzamido)cyclopropanecarboxylic acid (577 mg, 2.21 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (462 mg, 2.41 mmol) and 1-hydroxybenzotriazole hydrate (369 mg, 2.41 mmol) in dichloromethane (8 mL), add triethylamine (1.26 mL, 9.03 mmol) and stir the mixture at ambient temperature for approximately 16 hours. Purify the crude mixture by flash chromatography (0% to 5% MeOH/dichloromethane) to give the title compound (791 mg, 89%) as a tan foam: MS (m/z): 443 (M+1).

Workup

  1. customPurify the crude mixture by flash chromatography (0% to 5% MeOH/dichloromethane)

Sources & evidence

ORD record
ord-ca2191e02ca7434a8ead6138e42ce688
Source dataset
uspto-grants-2012_10
Patent number
US08299061B2

Reaction notes

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