trans-2-Phenyl-1-cyclopropanecarbonyl chloride → N-(7-chloro-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)-2-phenylcyclopropanecarboxamide

HRID 1409128Notes

Reaction equation

HRID 1409128 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 86652269N-(7-chloro-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)-2-phenylcyclopropanecarboxamideYield 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-8359888ae897426fa35dc1bfa01136b0
Source dataset
uspto-grants-2014_12
Patent number
US08921358B2

Reaction notes

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