Trifluoroacetic acid → 5-Fluoro-2-[5-(hexahydro-1,4-diazepin-1-yl)pyrazin-2-yl-carbonylamino]-N-(5-chloropyridin-2-yl)benzamide

HRID 1372877Notes

Reaction equation

HRID 1372877 reaction equation
C(OC([N:8]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[N:16]=[CH:17][C:18]([C:21]([NH:23][C:24]3[CH:39]=[CH:38][C:37]([F:40])=[CH:36][C:25]=3[C:26]([NH:28][C:29]3[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][N:30]=3)=[O:27])=[O:22])=[N:19][CH:20]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl.C1(OC)C=CC=CC=1>[F:40][C:37]1[CH:38]=[CH:39][C:24]([NH:23][C:21]([C:18]2[CH:17]=[N:16][C:15]([N:11]3[CH2:12][CH2:13][CH2:14][NH:8][CH2:9][CH2:10]3)=[CH:20][N:19]=2)=[O:22])=[C:25]([CH:36]=1)[C:26]([NH:28][C:29]1[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][N:30]=1)=[O:27]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 111806062-[5-(4-t-Butoxycarbonylhexahydro-1,4-diazepin-1-yl)pyrazin-2-ylcarbonylamino]-5-fluoro-N-(5-chloropyridin-2-yl)-benzamide

Product 1

HCID 98693075-Fluoro-2-[5-(hexahydro-1,4-diazepin-1-yl)pyrazin-2-yl-carbonylamino]-N-(5-chloropyridin-2-yl)benzamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7519AnisoleSolvent

Procedure

To a suspension of 2-[5-(4-t-butoxycarbonylhexahydro-1,4-diazepin-1-yl)pyrazin-2-ylcarbonylamino]-5-fluoro-N-(5-chloropyridin-2-yl)benzamide (Example P1, 11.4 g) in methylene chloride (30 mL) and anisole (10 mL) was added trifluoroacetic acid (30 mL) dropwise. The mixture was stirred overnight at room temperature before the solvent was evaporated. The residue was purified by using an SCX column. Yield 8.1 g.

Workup

  1. customwas evaporated
  2. customThe residue was purified

Sources & evidence

ORD record
ord-6a6db8c1d7d345a7925ee6236819d89b
Source dataset
uspto-grants-2007_01
Patent number
US07160878B2

Reaction notes

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