Trifluoroacetic acid → HCID 72950812, compound

HRID 1500879Notes

Reaction equation

HRID 1500879 reaction equation
[Cl:1][C:2]1[CH:40]=[CH:39][C:5]2[N:6]([CH:23]3[CH2:27][CH2:26][N:25]([C:28](=[O:38])[CH2:29][NH:30]C(=O)OC(C)(C)C)[CH2:24]3)[C:7]([CH2:9][N:10]3[C:14]4=[CH:15][N:16]=[CH:17][CH:18]=[C:13]4[C:12]([S:19]([CH3:22])(=[O:21])=[O:20])=[N:11]3)=[N:8][C:4]=2[CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:30][CH2:29][C:28]([N:25]1[CH2:26][CH2:27][CH:23]([N:6]2[C:5]3[CH:39]=[CH:40][C:2]([Cl:1])=[CH:3][C:4]=3[N:8]=[C:7]2[CH2:9][N:10]2[C:14]3=[CH:15][N:16]=[CH:17][CH:18]=[C:13]3[C:12]([S:19]([CH3:22])(=[O:20])=[O:21])=[N:11]2)[CH2:24]1)=[O:38]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89933258HCID 89933258, compound

Product 1

HCID 72950812HCID 72950812, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 2-(3-(5-chloro-2-((3-(methylsulfonyl)-1H-pyrazolo[3,4-c]pyridin-1-yl)methyl)-1H-benzo[d]imidazol-1-yl)pyrrolidin-1-yl)-2-oxoethylcarbamate(30 mg, 0.05 mmol) in 6 mL of DCM was added 3 mL of TFA. The mixture was stirred overnight. The solvent was removed in vacuum and purified by prep-HPLC to give product 2-amino-1-[3-(5-chloro-2-{[3-(methylsulfonyl)-1H-pyrazolo[3,4-c]pyridin-1-yl]methyl}-1H-benzimidazol-1-yl)pyrrolidin-1-yl]ethanone (10 mg, yield: 42%) as a pale solid.

Workup

  1. customThe solvent was removed in vacuum
  2. custompurified by prep-HPLC

Sources & evidence

ORD record
ord-2e583845aaba4bf1b24223c2ffa8083a
Source dataset
uspto-grants-2015_12
Patent number
US09206191B2

Reaction notes

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