Pyrazole → HCID 85472800, compound

HRID 1850705Notes

Reaction equation

HRID 1850705 reaction equation
[NH2:1][C:2]1[C:11]([C:12]([NH:14][C:15]2[S:19][N:18]=[C:17]([CH3:20])[C:16]=2Br)=[O:13])=[C:5]2[N:6]=[CH:7][C:8]([F:10])=[CH:9][N:4]2[N:3]=1.[NH:22]1[CH:26]=[CH:25][CH:24]=[N:23]1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[NH2:1][C:2]1[C:11]([C:12]([NH:14][C:15]2[S:19][N:18]=[C:17]([CH3:20])[C:16]=2[N:22]2[CH:26]=[CH:25][CH:24]=[N:23]2)=[O:13])=[C:5]2[N:6]=[CH:7][C:8]([F:10])=[CH:9][N:4]2[N:3]=1

Participants

5

Reactant 3

HCID 1048PyrazoleHCID 10796Cesium carbonateHCID 90411776HCID 90411776, compound

Product 1

HCID 85472800HCID 85472800, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 2-amino-N-(4-bromo-3-methyl-isothiazol-5-yl)-6-fluoro-pyrazolo[1,5-a]pyrimidine-3-carboxamide (20 mg, 0.05388 mmol), 1H-pyrazole (7.339 mg, 0.1078 mmol), Cut (21 mg, 0.1103 mmol), Cs2CO3 (71 mg, 0.2179 mmol) in DMF (2 mL) was degassed with nitrogen and heated at 140° C. in a microwave for 1 h. The insoluble material was filtered off and the filtrate was purified by fractionlynx. The clean fractions were freeze-dried yielding 2-amino-6-fluoro-N-(3-methyl-4-(1H-pyrazol-1-yl)isothiazol-5-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide as a pale yellow solid. (0.63 mg, 1.9%). MS (ES+) 359.1.

Workup

  1. customwas degassed with nitrogen
  2. filtrationThe insoluble material was filtered off
  3. customthe filtrate was purified by fractionlynx
  4. customThe clean fractions were freeze-dried

Sources & evidence

ORD record
ord-4ab0b56d4cb74d3e8a81ffe9b4ccc71a
Source dataset
uspto-grants-2015_02
Patent number
US08957078B2

Reaction notes

Loading…