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

HRID 474323Notes

Reaction equation

HRID 474323 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]([N:21]2[C:25]([NH2:26])=[CH:24][C:23]([CH3:27])=[N:22]2)[CH:18]=[CH:19][CH:20]=1.C(N(CC)C(C)C)(C)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[N:21]([C:17]4[CH:18]=[CH:19][CH:20]=[C:15]([Cl:14])[CH:16]=4)[N:22]=[C:23]([CH3:27])[CH:24]=3)=[O:12])=[C:4]2[N:3]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 18106301-(3-chlorophenyl)-3-methyl-1H-pyrazol-5-amineHCID 580631365-Chloropyrazolo[1,5-a]pyrimidine-3-carbonyl chloride

Product 1

HCID 580633975-chloro-N-(1-(3-chlorophenyl)-3-methyl-1H-pyrazol-5-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamideYield 95.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 5-chloropyrazolo[1,5-a]pyrimidine-3-carbonyl chloride (150 mg, 0.69 mM, 1.0 equiv), 1-(3-chlorophenyl)-3-methyl-1H-pyrazol-5-amine (140 mg, 0.69 mM, 1.0 equiv, available from Enamine, Ltd, Cincinnati, Ohio Cat# EN300-02447), N,N-diisopropylethylamine (0.18 mL, 1.0 mM, 1.0 equiv), and 15 mL of dichloromethane was stirred at ambient temperature for 3 days. The reaction was partitioned between dichloromethane and water. The dichloromethane phase was dried over sodium sulfate and vacuum filtered through silica gel. The silica gel pad was washed with 95:5 dichloromethane:methanol. The combined filtrates were concentrated to give 250 mg (93%) of 5-chloro-N-(1-(3-chlorophenyl)-3-methyl-1H-pyrazol-5-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide which was 74% pure by HPLC and used without further purification. LCMS (ESI) m+H=387.2, (two chlorine isotope pattern).

Workup

  1. customThe reaction was partitioned between dichloromethane and water
  2. dry with materialThe dichloromethane phase was dried over sodium sulfate and vacuum
  3. filtrationfiltered through silica gel
  4. washThe silica gel pad was washed with 95:5 dichloromethane
  5. concentrationThe combined filtrates were concentrated

Sources & evidence

ORD record
ord-41207d98790c41d3a04ec0ad628224f6
Source dataset
uspto-grants-2014_01
Patent number
US08637526B2

Reaction notes

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