trans-2-Phenyl-1-cyclopropanecarbonyl chloride → HCID 86652269, compound

HRID 1256287Notes

Reaction equation

HRID 1256287 reaction equation
[C:1]1([C@@H:7]2[CH2:9][C@H:8]2[C:10](Cl)=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:13][C:14]1[N:19]2[N:20]=[C:21]([CH3:23])[CH:22]=[C:18]2[N:17]=[C:16]([NH2:24])[CH:15]=1>N1C=CC=CC=1>[Cl:13][C:14]1[N:19]2[N:20]=[C:21]([CH3:23])[CH:22]=[C:18]2[N:17]=[C:16]([NH:24][C:10]([CH:8]2[CH2:9][CH:7]2[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[O:11])[CH:15]=1

Participants

4

Reactant 2

HCID 13656trans-2-Phenyl-1-cyclopropanecarbonyl chlorideHCID 442513077-Chloro-2-methylpyrazolo(1,5-a)pyrimidin-5-amine

Product 1

HCID 86652269HCID 86652269, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In a 250 ml round-bottomed flask was added (+/−)-trans-2-phenylcyclopropanecarbonyl chloride (1.9 g, 10 mmol) in pyridine (94 ml) to give a yellow suspension. 7-Chloro-2-methylpyrazolo[1,5-a]pyrimidin-5-amine (1J, 1.7 g, 9.4 mmol) was added portionwise at 0° C. The temperature was slowly raised to room temperature. After 30 min, reaction was complete and was quenched with saturated sodium bicarbonate solution. The layers were extracted with ethyl acetate (3×100 mL), and the organic layers were washed with saturated sodium bicarbonate solution and concentrated in vacuo. The residue was suspended in methanol and filtered. The filtrate was concentrated to obtain the product N-(7-chloro-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)-2-phenylcyclopropanecarboxamide (8C, 1.9 g, 62%) as an orange solid. 1H NMR (DMSO-d6) δ: 11.39 (s, 1H), 7.99 (s, 1H), 7.27-7.34 (m, 2H), 7.15-7.25 (m, 3H), 6.39 (s, 1H), 2.46 (td, 1H), 2.41 (s, 3H), 2.30-2.37 (m, 1H), 1.50-1.58 (m, 1H), 1.46 (ddd, J=8.2, 6.6, 4.2 Hz, 1H). ESI-MS: m/z 327.2 (M+H)+.

Workup

  1. customto give a yellow suspension
  2. customreaction
  3. customwas quenched with saturated sodium bicarbonate solution
  4. extractionThe layers were extracted with ethyl acetate (3×100 mL)
  5. washthe organic layers were washed with saturated sodium bicarbonate solution
  6. concentrationconcentrated in vacuo
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-7fd21c13fd5d4f77b1c438df359de165
Source dataset
uspto-grants-2013_06
Patent number
US08461163B2

Reaction notes

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