Ammonia → HCID 71539663, compound

HRID 1915879Notes

Reaction equation

HRID 1915879 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[S:10][C:11]([NH:33]C(=O)OC(C)(C)C)=[C:12]([C:14](=[O:32])[NH:15][C:16]2[CH:17]=[N:18][N:19]([CH3:31])[C:20]=2[N:21]2[CH2:26][CH2:25][NH:24][C@@H:23]([C:27]([F:30])([F:29])[F:28])[CH2:22]2)[N:13]=1.N>C(O)(C(F)(F)F)=O.C(Cl)Cl>[NH2:33][C:11]1[S:10][C:9]([C:3]2[C:2]([F:1])=[CH:7][CH:6]=[CH:5][C:4]=2[F:8])=[N:13][C:12]=1[C:14]([NH:15][C:16]1[CH:17]=[N:18][N:19]([CH3:31])[C:20]=1[N:21]1[CH2:26][CH2:25][NH:24][C@H:23]([C:27]([F:29])([F:30])[F:28])[CH2:22]1)=[O:32]

Participants

5

Reactant 2

HCID 222AmmoniaHCID 86680083HCID 86680083, compound

Product 1

HCID 71539663HCID 71539663, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of tert-Butyl (R)-2-(2,6-difluorophenyl)-4-(1-methyl-5-(3-(trifluoromethyl)piperazin-1-yl)-1H-pyrazol-4-ylcarbamoyl)thiazol-5-ylcarbamate (80 mg, 0.126 mmol) in TFA (1 mL) and DCM (4 mL) was stirred at ambient temperature for 3 hours. The pH of the mixture was adjusted to about 8˜9 by addition of ammonia and concentrated under reduced pressure to give a residue. The residue was purified by preparative HPLC to afford 169 formic acid salt (40 mg, 73%) as white solid. 1H NMR (500 MHz, DMSO-d6) δ (ppm): 8.84 (s, 1H), 7.50-7.55 (m, 3H), 7.37 (s, 1H), 7.25-7.28 (m, 2H), 3.47 (s, 3H), 3.36-3.48 (m, 1H), 3.07-3.16 (m, 3H), 2.94-2.96 (m, 2H), 2.78-2.80 (m, 1H), 1.24 (s, 1H); MS (ESI) m/z=488.1 (M+1+).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customto give a residue
  3. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-f84a5e7598ea48b28409c87cb5ddf909
Source dataset
uspto-grants-2013_12
Patent number
US08614206B2

Reaction notes

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