Pyridine → HCID 86652271, compound

HRID 1409135Notes

Reaction equation

HRID 1409135 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.N1C=CC=CC=1.[F:19][C:20]([F:32])([F:31])[O:21][C:22]1[CH:30]=[CH:29][C:25]([C:26](Cl)=[O:27])=[CH:24][CH:23]=1>>[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:26](=[O:27])[C:25]2[CH:29]=[CH:30][C:22]([O:21][C:20]([F:19])([F:31])[F:32])=[CH:23][CH:24]=2)[CH:3]=1

Participants

4

Reactant 3

HCID 1049PyridineHCID 1421104-(Trifluoromethoxy)benzoyl ChlorideHCID 442513077-Chloro-2-methylpyrazolo(1,5-a)pyrimidin-5-amine

Product 1

HCID 86652271HCID 86652271, compoundYield 51.3%

Conditions

Temperature
0 °C

Procedure

To a 20 mL scintillation vial was added 7-chloro-2-methylpyrazolo[1,5-a]pyrimidin-5-amine (1J, 0.207 g, 1.131 mmol) and pyridine (2.84 ml, 35.1 mmol) and the solution was cooled to 0° C. To the yellow solution was added 4-(trifluoromethoxy)benzoyl chloride (0.508 g, 2.262 mmol) to give an orange suspension. The reaction mixture was stirred for one hour, quenched by the addition of saturated aqueous sodium bicarbonate, and extracted with ethyl acetate. The organic extracts were dried over sodium sulfate, filtered, and concentrated under reduced pressure in the presence of silica gel. The silica-adsorbed material was then purified by silica gel chromatography (25-75% ethyl acetate/hexanes gradient) to afford the desired compound N-(7-chloro-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)-4-(trifluoromethoxy)benzamide 14A as an orange solid (215 mg, 51% yield); ESI-MS: m/z 370.0 (M+H)+.

Workup

  1. customto give an orange suspension
  2. customquenched by the addition of saturated aqueous sodium bicarbonate
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure in the presence of silica gel
  7. customThe silica-adsorbed material was then purified by silica gel chromatography (25-75% ethyl acetate/hexanes gradient)

Sources & evidence

ORD record
ord-c8e40cf87df240ccba06332bf503a21a
Source dataset
uspto-grants-2014_12
Patent number
US08921358B2

Reaction notes

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