Trifluoroacetic acid → 2,6-difluoro-N-{2-fluoro-3-[2-(4-methyl-4-piperidinyl)-5-(2-methyl-4-pyrimidinyl)-1,3-thiazol-4-yl]phenyl}benzenesulfonamide

HRID 1962077Notes

Reaction equation

HRID 1962077 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[S:9]([NH:12][C:13]1[C:14]([F:45])=[C:15]([C:19]2[N:20]=[C:21]([C:31]3([CH3:44])[CH2:36][CH2:35][N:34](C(OC(C)(C)C)=O)[CH2:33][CH2:32]3)[S:22][C:23]=2[C:24]2[CH:29]=[CH:28][N:27]=[C:26]([CH3:30])[N:25]=2)[CH:16]=[CH:17][CH:18]=1)(=[O:11])=[O:10].C(O)(C(F)(F)F)=O>ClCCl>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[S:9]([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19]2[N:20]=[C:21]([C:31]3([CH3:44])[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]3)[S:22][C:23]=2[C:24]2[CH:29]=[CH:28][N:27]=[C:26]([CH3:30])[N:25]=2)[C:14]=1[F:45])(=[O:10])=[O:11]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 579898041,1-Dimethylethyl 4-[4-(3-{[(2,6-difluorophenyl)sulfonyl]amino}-2-fluorophenyl)-5-(2-methyl-4-pyrimidinyl)-1,3-thiazol-2-yl]-4-methyl-1-piperidinecarboxylate

Product 1

HCID 579899592,6-difluoro-N-{2-fluoro-3-[2-(4-methyl-4-piperidinyl)-5-(2-methyl-4-pyrimidinyl)-1,3-thiazol-4-yl]phenyl}benzenesulfonamideYield 62.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,1-dimethylethyl 4-[4-(3-{[(2,6-difluorophenyl)sulfonyl]amino}-2-fluorophenyl)-5-(2-methyl-4-pyrimidinyl)-1,3-thiazol-2-yl]-4-methyl-1-piperidinecarboxylate (72 mg, 0.109 mmol) in dichloromethane (2 mL) was added TFA (0.5 mL, 6.49 mmol), and the reaction mixture was stirred for 1 h. The reaction was concentrated and the residue was purified using RP-HPLC. The TFA salt was neutralized to obtain the title compound (38 mg). MS (ESI): 560.0 [M+1]+.

Workup

  1. concentrationThe reaction was concentrated
  2. customthe residue was purified

Sources & evidence

ORD record
ord-06b699e0aa254303b9f1127057952309
Source dataset
uspto-grants-2013_04
Patent number
US08415345B2

Reaction notes

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