3-Cyclopentylpropionyl chloride → 3-cyclopentyl-N-(3-isopropylpyrazolo[1,5-a]pyrimidin-2-yl)propanamide

HRID 1912916Notes

Reaction equation

HRID 1912916 reaction equation
[CH:1]1([CH2:6][CH2:7][C:8](Cl)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:11]([C:14]1[C:15]([NH2:23])=[N:16][N:17]2[CH:22]=[CH:21][CH:20]=[N:19][C:18]=12)([CH3:13])[CH3:12]>C(Cl)Cl.N1C=CC=CC=1>[CH:1]1([CH2:6][CH2:7][C:8]([NH:23][C:15]2[C:14]([CH:11]([CH3:13])[CH3:12])=[C:18]3[N:19]=[CH:20][CH:21]=[CH:22][N:17]3[N:16]=2)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 660393-Cyclopentylpropionyl chlorideHCID 687533643-Isopropylpyrazolo[1,5-a]pyrimidin-2-amine

Product 1

HCID 687500223-cyclopentyl-N-(3-isopropylpyrazolo[1,5-a]pyrimidin-2-yl)propanamide

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 3-cyclopentylpropionyl chloride (0.048 mL, 0.31 mmol) in CH2Cl2 (0.2 mL) was added to a stirring solution of the product from Example 112C (35 mg, 0.20 mmol) in pyridine (1.2 mL) in a 4 mL vial. The yellow solution was stirred at room temperature for 3 hours, and then concentrated under vacuum. The residue was dissolved in CH2Cl2 (3 mL) and concentrated under vacuum (repeated three times) to remove excess pyridine. The off-white solid residue was crystallized from 60% ethanol-water (8 mL) to provide the title compound. 1H NMR (300 MHz, CD3OD) δ ppm 1.10-1.27 (m, 2H) 1.41 (d, J=7.1 Hz, 6H) 1.48-1.98 (m, 9H) 2.47 (t, J=7.6 Hz, 2H) 3.01-3.22 (m, 1H) 6.91 (dd, J=7.1, 4.1 Hz, 1H) 8.42 (dd, J=4.1, 2.0 Hz, 1H) 8.70 (dd, J=7.1, 1.7 Hz, 1H); MS (ESI) m/z 301 (M+H)+; Anal. Calculated for C17H24N4O: C, 67.97; H, 8.05; N, 18.65. Found: C, 68.03; H, 8.03; N, 18.60.

Workup

  1. concentrationconcentrated under vacuum
  2. dissolutionThe residue was dissolved in CH2Cl2 (3 mL)
  3. concentrationconcentrated under vacuum (repeated three times)
  4. customto remove excess pyridine
  5. customThe off-white solid residue was crystallized from 60% ethanol-water (8 mL)

Sources & evidence

ORD record
ord-83923c31e7a54bd48a6c6cbf4264d8b4
Source dataset
uspto-grants-2013_12
Patent number
US08609669B2

Reaction notes

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