Pyridine → 5-[Acetyl-(3,5-bis-trifluoromethyl-benzyl)-amino]-9-methyl-7-trifluoromethyl-2,3,4,5-tetrahydro-benzo[b]azepine-1-carboxylic acid isopropyl ester

HRID 2353919Notes

Reaction equation

HRID 2353919 reaction equation
[F:1][C:2]([F:35])([F:34])[C:3]1[CH:4]=[C:5]([CH:27]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:29]=1)[CH2:6][N:7]([CH:11]1[CH2:17][CH2:16][CH2:15][NH:14][C:13]2[C:18]([CH3:26])=[CH:19][C:20]([C:22]([F:25])([F:24])[F:23])=[CH:21][C:12]1=2)[C:8](=[O:10])[CH3:9].N1C=CC=CC=1.[CH:42]([O:45][C:46](Cl)=[O:47])([CH3:44])[CH3:43]>ClCCl>[CH:42]([O:45][C:46]([N:14]1[CH2:15][CH2:16][CH2:17][CH:11]([N:7]([C:8](=[O:10])[CH3:9])[CH2:6][C:5]2[CH:4]=[C:3]([C:2]([F:1])([F:34])[F:35])[CH:29]=[C:28]([C:30]([F:32])([F:33])[F:31])[CH:27]=2)[C:12]2[CH:21]=[C:20]([C:22]([F:23])([F:24])[F:25])[CH:19]=[C:18]([CH3:26])[C:13]1=2)=[O:47])([CH3:44])[CH3:43]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7917Isopropyl chloroformateHCID 86616073N-(3,5-Bis-trifluoromethyl-benzyl)-N-(9-methyl-7-trifluoromethyl-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl)-acetamide

Product 1

HCID 866160755-[Acetyl-(3,5-bis-trifluoromethyl-benzyl)-amino]-9-methyl-7-trifluoromethyl-2,3,4,5-tetrahydro-benzo[b]azepine-1-carboxylic acid isopropyl esterYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(3,5-Bis-trifluoromethyl-benzyl)-N-(9-methyl-7-trifluoromethyl-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl)-acetamide (0.0210 g, 0.0410 mmol) and pyridine (0.0100 ml, 0.123 mmol) in dichloromethane (1.00 ml) was added 1M isopropylchloroformate (solution in toluene) (0.120 ml), 0.123 mmol) dropwise. The mixture was stirred at room temperature overnight. The solvents were evaporated on a rotavapor (rotary evaporator). Purification by silica gel chromatography (gradient eluent, 0-30% ethyl acetate in hexane) provided the titled compound (0.0180 g, 72%) as white crystalline. MS (ES+): 599 (M+H).

Workup

  1. customThe solvents were evaporated on a rotavapor (rotary evaporator)
  2. customPurification by silica gel chromatography (gradient eluent, 0-30% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-6cb43dc38f4f47c49ba7cf7dd8b46eb8
Source dataset
uspto-grants-2010_07
Patent number
US07749992B2

Reaction notes

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