Benzenepropanoyl chloride → N-[3-(4-chloro-3-methylphenyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-2-yl]-3-phenylpropanamide

HRID 1912900Notes

Reaction equation

HRID 1912900 reaction equation
[C:1]1([CH2:7][CH2:8][C:9](Cl)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[C:20]([NH2:30])=[N:21][N:22]3[C:27]([CH3:28])=[CH:26][C:25]([CH3:29])=[N:24][C:23]=23)=[CH:15][C:14]=1[CH3:31]>N1C=CC=CC=1>[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[C:20]([NH:30][C:9](=[O:10])[CH2:8][CH2:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[N:21][N:22]3[C:27]([CH3:28])=[CH:26][C:25]([CH3:29])=[N:24][C:23]=23)=[CH:15][C:14]=1[CH3:31]

Participants

4

Reactant 2

HCID 64801Benzenepropanoyl chlorideHCID 687470433-(4-Chloro-3-methylphenyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-2-amine

Product 1

HCID 68751193N-[3-(4-chloro-3-methylphenyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-2-yl]-3-phenylpropanamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3-Phenylpropionyl chloride (0.078 mL, 0.53 mmol) was added to a stirring solution of the product from Example 47C (85 mg, 0.296 mmol) in pyridine (5 mL), and the mixture was stirred at room temperature for 12 hours. The mixture was concentrated under vacuum, and the residue diluted with MeOH (5 mL) and stirred for 30 minutes at room temperature. The mixture was concentrated under vacuum and the residue was crystallized from 80% aqueous ethanol (15 mL) to provide the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 2.34 (s, 3H) 2.53 (s, 3H) 2.60-2.69 (m, 2H) 2.66 (s, 3H) 2.87 (t, J=7.6 Hz, 2H) 6.98 (d, J=0.7 Hz, 1H) 7.14-7.32 (m, 5H) 7.38 (d, J=8.5 Hz, 1H) 7.56 (dd, J=8.5, 2.0 Hz, 1H) 7.72 (d, J=1.7 Hz, 1H) 10.21 (s, 1H); MS (ESI) m/z 419/421 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated under vacuum
  2. additionthe residue diluted with MeOH (5 mL)
  3. stirringstirred for 30 minutes at room temperature
  4. concentrationThe mixture was concentrated under vacuum
  5. customthe residue was crystallized from 80% aqueous ethanol (15 mL)

Sources & evidence

ORD record
ord-0ad7ed221e884584958592494fca8885
Source dataset
uspto-grants-2013_12
Patent number
US08609669B2

Reaction notes

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