Trifluoroacetic acid → HCID 71532822, compound

HRID 2274956Notes

Reaction equation

HRID 2274956 reaction equation
C([O:5][CH2:6][C:7]([N:9]1[CH2:14][CH2:13][C:12]2[N:15]([CH2:26][C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][C:28]=3[F:34])[N:16]=[C:17]([C:18]3[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=3)[C:21]#[N:22])[C:11]=2[CH2:10]1)=[O:8])(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[F:34][C:28]1[CH:29]=[C:30]([F:33])[CH:31]=[CH:32][C:27]=1[CH2:26][N:15]1[C:12]2[CH2:13][CH2:14][N:9]([C:7](=[O:8])[CH2:6][OH:5])[CH2:10][C:11]=2[C:17]([C:18]2[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=2)[C:21]#[N:22])=[N:16]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 71533438HCID 71533438, compound

Product 1

HCID 71532822HCID 71532822, compoundYield 60.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-[5-(2-tert-Butoxy-acetyl)-1-(2,4-difluoro-benzyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridin-3-yl]-benzonitrile (8d) (90 mg, 0.193 mmol) and trifluoroacetic acid (221 mg, 1.94 mmol) in CH2Cl2 was stirred at 25° C. for 1 day. Solvents were evaporated and the residue purified by reverse phase HPLC (CH3CN/water gradient with 0.1% trifluoroacetic acid) to give 48 mg of 3-[1-(2,4-Difluoro-benzyl)-5-(2-hydroxy-acetyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridin-3-yl]-benzonitrile (14a).

Workup

  1. customSolvents were evaporated
  2. customthe residue purified by reverse phase HPLC (CH3CN/water gradient with 0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-bc8cdec114d9414baae222b2374f834f
Source dataset
uspto-grants-2015_09
Patent number
US09127001B2

Reaction notes

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