N-methyl-2-pyrrolidone → N-(7-chloro-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)-6-(trifluoromethyl)nicotinamide

HRID 1256293Notes

Reaction equation

HRID 1256293 reaction equation
[Cl:1][C:2]1[N:7]2[N:8]=[C:9]([CH3:11])[CH:10]=[C:6]2[N:5]=[C:4]([NH2:12])[CH:3]=1.[F:13][C:14]([F:25])([F:24])[C:15]1[CH:23]=[CH:22][C:18]([C:19](Cl)=[O:20])=[CH:17][N:16]=1.CN1C(=O)CCC1>O>[Cl:1][C:2]1[N:7]2[N:8]=[C:9]([CH3:11])[CH:10]=[C:6]2[N:5]=[C:4]([NH:12][C:19](=[O:20])[C:18]2[CH:22]=[CH:23][C:15]([C:14]([F:25])([F:13])[F:24])=[N:16][CH:17]=2)[CH:3]=1

Participants

5

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 27775576-(Trifluoromethyl)nicotinoyl chlorideHCID 442513077-Chloro-2-methylpyrazolo(1,5-a)pyrimidin-5-amine

Product 1

HCID 86652270N-(7-chloro-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)-6-(trifluoromethyl)nicotinamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 20 ml scintillation vial was added 7-chloro-2-methylpyrazolo[1,5-a]pyrimidin-5-amine (1.1, 237 mg, 1.30 mmol), 6-(trifluoromethyl)nicotinoyl chloride (328 mg, 1.57 mmol), and NMP (5 mL) and the reaction mixture was stirred at rt for 1 hr. The reaction mixture was then diluted with water, filtered, and the filter cake rinsed thoroughly with water. Drying with suction under a stream of dry nitrogen resulted in the desired product N-(7-chloro-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)-6-(trifluoromethyl)nicotinamide (12A) as a pink solid. 1H NMR (DMSO-d6) δ: 11.87 (s, 1H), 9.29 (d, J=2.3 Hz, 1H), 8.62 (dd, J=8.0, 1.9 Hz, 1H), 8.11 (d, J=8.3 Hz, 1H), 8.04 (s, 1H), 6.51 (s, 1H), 2.46 (s, 3H); ESI-MS: m/z 356.1 (M+H)+.

Workup

  1. filtrationfiltered
  2. washthe filter cake rinsed thoroughly with water
  3. customDrying with suction under a stream of dry nitrogen

Sources & evidence

ORD record
ord-621c00d4f9a546aa91ded41a003e3f48
Source dataset
uspto-grants-2013_06
Patent number
US08461163B2

Reaction notes

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