Water → HCID 136253985, compound

HRID 1043958Notes

Reaction equation

HRID 1043958 reaction equation
F[C:2]1[CH:7]=[C:6]([C:8]2[C:9]([O:16][CH3:17])=[N:10][C:11]([CH3:15])=[CH:12][C:13]=2[CH3:14])[C:5]([F:18])=[CH:4][C:3]=1[C:19]1[N:23]([CH:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)[N:22]=[CH:21][C:20]=1[C:30]([NH2:32])=[O:31].[Cl-].[NH4+].O>CN1C(=O)CCC1>[F:18][C:5]1[C:6]([C:8]2[C:9]([O:16][CH3:17])=[N:10][C:11]([CH3:15])=[CH:12][C:13]=2[CH3:14])=[CH:7][C:2]2[NH:32][C:30](=[O:31])[C:20]3[CH:21]=[N:22][N:23]([CH:24]4[CH2:29][CH2:28][O:27][CH2:26][CH2:25]4)[C:19]=3[C:3]=2[CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 86686391HCID 86686391, compound

Product 1

HCID 136253985HCID 136253985, compoundYield 73.7%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
90 °C

Procedure

KTB (41 mg) was added to a solution of 5-(2,5-difluoro-4-(2-methoxy-4,6-dimethylpyridin-3-yl)phenyl)-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazole-4-carboxamide (81 mg) in NMP (0.4 mL), and the mixture was heated to 90° C. After one hour, KTB (20 mg) was further added, followed by stirring for 30 minutes. The reaction mixture was cooled to room temperature, followed by adding a saturated aqueous ammonium chloride solution (2 mL) and water (1 mL). The generated solid was filtered off, washed with water (2 mL) and dried under reduced pressure at 60° C. to give the title compound (57 mg).

Workup

  1. additionKTB (20 mg) was further added
  2. temperatureThe reaction mixture was cooled to room temperature
  3. filtrationThe generated solid was filtered off
  4. washwashed with water (2 mL)
  5. customdried under reduced pressure at 60° C.

Sources & evidence

ORD record
ord-a4fe5b39cb4f4892835358e8a67c26aa
Source dataset
uspto-grants-2013_10
Patent number
US08563565B2

Reaction notes

Loading…