3-cyclopropylpropanoyl Chloride → 3-cyclopropyl-N-(3-isopropylpyrazolo[1,5-a]pyrimidin-2-yl)propanamide

HRID 1912923Notes

Reaction equation

HRID 1912923 reaction equation
[CH:1]1([CH2:4][CH2:5][C:6](Cl)=[O:7])[CH2:3][CH2:2]1.[CH:9]([C:12]1[C:13]([NH2:21])=[N:14][N:15]2[CH:20]=[CH:19][CH:18]=[N:17][C:16]=12)([CH3:11])[CH3:10]>C(Cl)Cl.N1C=CC=CC=1>[CH:1]1([CH2:4][CH2:5][C:6]([NH:21][C:13]2[C:12]([CH:9]([CH3:11])[CH3:10])=[C:16]3[N:17]=[CH:18][CH:19]=[CH:20][N:15]3[N:14]=2)=[O:7])[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 117080633-cyclopropylpropanoyl ChlorideHCID 687533643-Isopropylpyrazolo[1,5-a]pyrimidin-2-amine

Product 1

HCID 687514553-cyclopropyl-N-(3-isopropylpyrazolo[1,5-a]pyrimidin-2-yl)propanamide

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of the product from Example 114D (100 mg, 0.754 mmol) in CH2Cl2 (0.5 mL) was added to a stirring solution of the product from Example 112C (109 mg, 0.62 mmol) in pyridine (1.0 mL) at room temperature. The solution was stirred at room temperature for 2 hours, and then quenched by addition of methanol (0.5 mL). After 30 minutes, the solution was concentrated under vacuum, and the residue was purified by flash chromatography (silica gel, eluted with EtOAc), followed by crystallization from 80% EtOH-water to provide the title compound. 1H NMR (300 MHz, CD3OD) δ ppm 0.07-0.18 (m, 2H) 0.40-0.53 (m, 2H) 0.71-0.89 (m, 1H) 1.41 (d, J=7.1 Hz, 6H) 1.63 (q, J=7.2 Hz, 2H) 2.55 (t, J=7.5 Hz, 2H) 3.14 (hept, J=7.1 Hz, 1H) 6.91 (dd, J=7.0, 4.2 Hz, 1H) 8.42 (dd, J=4.1, 1.7 Hz, 1H) 8.70 (dd, J=7.1, 1.7 Hz, 1H) MS (ESI) m/z 273 (M+H)+; Anal. Calculated for C15H20N4O: C, 66.15; H, 7.40; N, 20.57. Found: C, 66.39; H, 7.28; N, 20.26.

Workup

  1. customquenched by addition of methanol (0.5 mL)
  2. waitAfter 30 minutes
  3. concentrationthe solution was concentrated under vacuum
  4. customthe residue was purified by flash chromatography (silica gel, eluted with EtOAc)
  5. customfollowed by crystallization from 80% EtOH-water

Sources & evidence

ORD record
ord-5497c2e314c74ade989cdf0cbee6d5a1
Source dataset
uspto-grants-2013_12
Patent number
US08609669B2

Reaction notes

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