Water → HCID 21865220, compound

HRID 857691Notes

Reaction equation

HRID 857691 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([O:8][C:9]2[C:14]3[N:15]=[C:16]([NH2:18])[S:17][C:13]=3[CH:12]=[CH:11][CH:10]=2)[CH:3]=1.C([O-])([O-])=O.[K+].[K+].Cl.[F:26][C:27]([F:35])([F:34])[CH:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1.O>CN(C=O)C>[F:26][C:27]([F:35])([F:34])[CH:28]1[CH2:33][CH2:32][N:31]([C:2]2[N:7]=[CH:6][N:5]=[C:4]([O:8][C:9]3[C:14]4[N:15]=[C:16]([NH2:18])[S:17][C:13]=4[CH:12]=[CH:11][CH:10]=3)[CH:3]=2)[CH2:30][CH2:29]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 162181604-(Trifluoromethyl)piperidine hydrochlorideHCID 21865284HCID 21865284, compound

Product 1

HCID 21865220HCID 21865220, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4-(6-chloro-pyrimidin-4-yloxy)-benzothiazol-2-ylamine, (Example 133(a)), (300 mg, 1.1 mmol) in dry DMF (3.0 mL) stirred at room temperature was added K2CO3 (590 mg, 4.3 mmol) and 4-(trifluoromethyl)piperidine hydrochloride (410 mg, 2.1 mmol, Matrix Scientific). The reaction mixture was stirred at 80° C. for 4 h. The resulting mixture was allowed to cool to room temperature and treated with water (20 mL). The resulting precipitate was collected by filtration, washed with water (2×), MeOH (1×), and EtOAc (3×), then dried in vacuum. The title compound was obtained as a white amorphous solid. MS (ESI, pos. ion) m/z: 396 (N+1). Anal. Calcd for C17H16F3N5OS: C, 51.64; H, 4.08; N, 17.71; F, 14.41. Found: C, 51.62; H, 4.09; N, 17.61; F, 14.33.

Workup

  1. temperatureto cool to room temperature
  2. filtrationThe resulting precipitate was collected by filtration
  3. washwashed with water (2×), MeOH (1×), and EtOAc (3×)
  4. customdried in vacuum

Sources & evidence

ORD record
ord-2bd25c6016634553a9e39aa118d9fae0
Source dataset
uspto-grants-2006_12
Patent number
US07144888B2

Reaction notes

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