Trifluoroacetic acid → 4-(4-Methylpiperazin-1-yl)-2-(2,2,2-trifluoro-N-(tetrahydro-2H-pyran-4-yl)acetamido)benzoic acid 2,2,2-trifluoroacetate

HRID 1640977Notes

Reaction equation

HRID 1640977 reaction equation
C([O:5][C:6](=[O:33])[C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]2)=[CH:9][C:8]=1[N:20]([CH:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1)[C:21](=[O:26])[C:22]([F:25])([F:24])[F:23])(C)(C)C.[F:34][C:35]([F:40])([F:39])[C:36]([OH:38])=[O:37]>ClCCl>[F:34][C:35]([F:40])([F:39])[C:36]([OH:38])=[O:37].[CH3:19][N:16]1[CH2:15][CH2:14][N:13]([C:10]2[CH:11]=[CH:12][C:7]([C:6]([OH:33])=[O:5])=[C:8]([N:20]([CH:27]3[CH2:28][CH2:29][O:30][CH2:31][CH2:32]3)[C:21](=[O:26])[C:22]([F:24])([F:25])[F:23])[CH:9]=2)[CH2:18][CH2:17]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86643836Tert-butyl 4-(4-methylpiperazin-1-yl)-2-(oxan-4-yl-(2,2,2-trifluoroacetyl)amino)benzoate

Product 1

HCID 866438384-(4-Methylpiperazin-1-yl)-2-(2,2,2-trifluoro-N-(tetrahydro-2H-pyran-4-yl)acetamido)benzoic acid 2,2,2-trifluoroacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-(4-methyl-piperazin-1-yl)-2-[(tetrahydro-pyran-4-yl)-(2,2,2-trifluoro-acetyl)-amino]-benzoic acid tert-butyl ester (12.1 g, 25.7 mmol), trifluoroacetic acid (48.5 mL) and dichloromethane (195 mL) was stirred at room temperature for 2 hours. The volatiles were then evaporated, the residue taken up with diethylether and evaporated again. The procedure was repeated 5 times, then the solid was triturated with diethylether, filtered and dried in oven at 40° C. affording the title compound as a pale brown solid (13.4 g).

Workup

  1. customThe volatiles were then evaporated
  2. customevaporated again
  3. customthe solid was triturated with diethylether
  4. filtrationfiltered
  5. customdried in oven at 40° C.

Sources & evidence

ORD record
ord-bee6e31cbaa94daab6d12621b2ec0cd7
Source dataset
uspto-grants-2012_02
Patent number
US08114865B2

Reaction notes

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