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 628970Notes

Reaction equation

HRID 628970 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:14]3[CH:15]=[C:16]([O:19][CH3:20])[CH:17]=[CH:18][C:13]=3[N:12]3[C:21]([CH3:24])=[N:22][N:23]=[C:11]3[C@H:10]([CH2:25][C:26]([NH:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][NH:34]C(=O)OC(C)(C)C)=[O:27])[N:9]=2)=[CH:4][CH:3]=1.[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].[NH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][NH:28][C:26](=[O:27])[CH2:25][C@@H:10]1[N:9]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[C:14]2[CH:15]=[C:16]([O:19][CH3:20])[CH:17]=[CH:18][C:13]=2[N:12]2[C:21]([CH3:24])=[N:22][N:23]=[C:11]12

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68186050HCID 68186050, 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-c3abccf735754393bb4b2478c5d36076
Source dataset
uspto-grants-2016_04
Patent number
US09315487B2

Reaction notes

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