Trifluoroacetic acid → N-(5-aminopentyl)-2[(4S)-6-(4-chlorophenyl)-1-methyl-8-(methyloxy)-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-4-yl]acetamide trifluoroacetate

HRID 82019Notes

Reaction equation

HRID 82019 reaction equation
CC([N:5]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][NH:14][C:15](=[O:41])[CH2:16][C@@H:17]1[N:23]=[C:22]([C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=2)[C:21]2[CH:31]=[C:32]([O:35][CH3:36])[CH:33]=[CH:34][C:20]=2[N:19]2[C:37]([CH3:40])=[N:38][N:39]=[C:18]12)C(=O)[O-])(C)C.[F:42][C:43]([F:48])([F:47])[C:44]([OH:46])=[O:45]>ClCCl>[F:42][C:43]([F:48])([F:47])[C:44]([OH:46])=[O:45].[NH2:5][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][NH:14][C:15](=[O:41])[CH2:16][C@@H:17]1[N:23]=[C:22]([C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=2)[C:21]2[CH:31]=[C:32]([O:35][CH3:36])[CH:33]=[CH:34][C:20]=2[N:19]2[C:37]([CH3:40])=[N:38][N:39]=[C:18]12

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86669137HCID 86669137, compound

Product 1

HCID 52934591N-(5-aminopentyl)-2[(4S)-6-(4-chlorophenyl)-1-methyl-8-(methyloxy)-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-4-yl]acetamide trifluoroacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,1-dimethylethyl[5-({[(4S)-6-(4-chlorophenyl)-1-methyl-8-(methyloxy)-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-4-yl]acetyl}amino)pentyl]carbamate (for a preparation see Reference compound H) (0.2 g, 0.34 mmol) in dichloromethane (3 ml) was added trifluoroacetic acid (0.053 ml, 0.68 mmol) dropwise at 0° C. The reaction mixture was stirred for 3 h from 0° C. to room temperature. The reaction mixture was concentrated to dryness to afford the title compound as a hygroscopic yellow oil (200 mg)

Workup

  1. concentrationThe reaction mixture was concentrated to dryness

Sources & evidence

ORD record
ord-f043687048074a309edec08e3eca9285
Source dataset
uspto-grants-2014_09
Patent number
US08846709B2

Reaction notes

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