Triethylamine → HCID 178424879, compound

HRID 474333Notes

Reaction equation

HRID 474333 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.[CH3:14][C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][C:16]=1[C:22]1[C:26]([NH2:27])=[CH:25][NH:24][N:23]=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:27][C:26]3[C:22]([C:16]4[CH:17]=[C:18]([CH3:21])[CH:19]=[CH:20][C:15]=4[CH3:14])=[N:23][NH:24][CH:25]=3)=[O:12])=[C:4]2[N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 580631365-Chloropyrazolo[1,5-a]pyrimidine-3-carbonyl chlorideHCID 178424878HCID 178424878, compound

Product 1

HCID 178424879HCID 178424879, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-chloropyrazolo[1,5-a]pyrimidine-3-carbonyl chloride (400.4 mg, 1.853 mmol, 1.16 equiv) in dichloromethane (6 mL) was added 3-(2,5-dimethylphenyl)-1H-pyrazol-4-amine (300.0 mg, 1.602 mmol, 1.0 equiv) and triethylamine (0.70 mL, 5.0 mmol, 3.1 equiv) at room temperature. After 14 hours, the reaction mixture was partitioned between dichloromethane and half-saturated aqueous sodium bicarbonate solution. The aqueous layer was extracted once with dichloromethane. The combined organic portions are dried over magnesium sulfate, filtered, and concentrated to yield 5-chloro-N-(3-(2,5-dimethylphenyl)-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide, which was carried forward without purification. LCMS (ESI) m+H=367.1.

Workup

  1. customthe reaction mixture was partitioned between dichloromethane and half-saturated aqueous sodium bicarbonate solution
  2. extractionThe aqueous layer was extracted once with dichloromethane
  3. dry with materialThe combined organic portions are dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8028ffad180946d7aa83e75a761dec24
Source dataset
uspto-grants-2014_01
Patent number
US08637526B2

Reaction notes

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