Triethylamine → 5-chloro-N-(3-(3-chlorophenyl)-1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide

HRID 474338Notes

Reaction equation

HRID 474338 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]2[N:8]=[CH:9][C:10]([C:11](Cl)=[O:12])=[C:4]2[N:3]=1.[Cl:14][C:15]1[CH:16]=[C:17]([C:21]2[C:25]([NH2:26])=[CH:24][N:23]([CH3:27])[N:22]=2)[CH:18]=[CH:19][CH:20]=1.C(N(CC)CC)C>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]2[N:8]=[CH:9][C:10]([C:11]([NH:26][C:25]3[C:21]([C:17]4[CH:18]=[CH:19][CH:20]=[C:15]([Cl:14])[CH:16]=4)=[N:22][N:23]([CH3:27])[CH:24]=3)=[O:12])=[C:4]2[N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 580631365-Chloropyrazolo[1,5-a]pyrimidine-3-carbonyl chlorideHCID 580634153-(3-chlorophenyl)-1-methyl-1H-pyrazol-4-amine

Product 1

HCID 715122515-chloro-N-(3-(3-chlorophenyl)-1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-chloropyrazolo[1,5-a]pyrimidine-3-carbonyl chloride (0.166 g, 0.768 mmol) in dichloromethane (8 mL) was added 3-(3-chlorophenyl)-1-methyl-1H-pyrazol-4-amine (73.6 mg, 0.354 mmol) and triethylamine (0.20 mL, 1.4 mmol) at room temperature. After 1 hour, the reaction mixture was partitioned between dichloromethane and half-saturated aqueous sodium bicarbonate solution. The organic layer was dried over magnesium sulfate and concentrated to yield 5-chloro-N-(3-(3-chlorophenyl)-1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide, which is carried forward without purification. LCMS (ESI) m+H=387.1.

Workup

  1. customthe reaction mixture was partitioned between dichloromethane and half-saturated aqueous sodium bicarbonate solution
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-4d1010f529f14f10908305a20a0fe71e
Source dataset
uspto-grants-2014_01
Patent number
US08637526B2

Reaction notes

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