3,3-Dimethylbutanoyl chloride → N-(3-isopropylpyrazolo[1,5-a]pyrimidin-2-yl)-3,3-dimethylbutanamide

HRID 1912917Notes

Reaction equation

HRID 1912917 reaction equation
[CH3:1][C:2]([CH3:8])([CH3:7])[CH2:3][C:4](Cl)=[O:5].[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:9]([C:12]1[C:13]([NH:21][C:4](=[O:5])[CH2:3][C:2]([CH3:8])([CH3:7])[CH3:1])=[N:14][N:15]2[CH:20]=[CH:19][CH:18]=[N:17][C:16]=12)([CH3:11])[CH3:10]

Participants

5

Reactant 2

HCID 815143,3-Dimethylbutanoyl chlorideHCID 687533643-Isopropylpyrazolo[1,5-a]pyrimidin-2-amine

Product 1

HCID 68750992N-(3-isopropylpyrazolo[1,5-a]pyrimidin-2-yl)-3,3-dimethylbutanamideYield 72.9%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 3,3-dimethylbutanoyl chloride (0.043 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 (4 mL) and concentrated under vacuum to remove excess pyridine. The residue was crystallized from 60% ethanol-water (10 mL) to provide the title compound (40 mg). 1H NMR (300 MHz, CD3OD) δ ppm 1.13 (s, 9H) 1.31-1.53 (m, 6H) 2.33 (s, 2H) 2.95-3.24 (m, 1H) 6.91 (dd, J=7.0, 4.2 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 275 (M+H)+; Anal. Calculated for C15H22N4O: C, 65.67; H, 8.08; N, 20.42. Found: C, 65.74; H, 8.10; N, 20.46.

Workup

  1. concentrationconcentrated under vacuum
  2. dissolutionThe residue was dissolved in CH2Cl2 (4 mL)
  3. concentrationconcentrated under vacuum
  4. customto remove excess pyridine
  5. customThe residue was crystallized from 60% ethanol-water (10 mL)

Sources & evidence

ORD record
ord-9669ff3e216b4c46a8f0998272bed865
Source dataset
uspto-grants-2013_12
Patent number
US08609669B2

Reaction notes

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