3-(4-Chloro-3-methylphenyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-2-amine → N-[3-(4-chloro-3-methylphenyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-2-yl]-2-(cyclopentyloxy)acetamide

HRID 1912939Notes

Reaction equation

HRID 1912939 reaction equation
[CH:1]1([O:6][CH2:7][C:8](Cl)=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[C:19]([NH2:29])=[N:20][N:21]3[C:26]([CH3:27])=[CH:25][C:24]([CH3:28])=[N:23][C:22]=23)=[CH:14][C:13]=1[CH3:30]>N1C=CC=CC=1>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[C:19]([NH:29][C:8](=[O:9])[CH2:7][O:6][CH:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)=[N:20][N:21]3[C:26]([CH3:27])=[CH:25][C:24]([CH3:28])=[N:23][C:22]=23)=[CH:14][C:13]=1[CH3:30]

Participants

4

Reactant 2

HCID 687470433-(4-Chloro-3-methylphenyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-2-amineHCID 866419172-(Cyclopentyloxy)acetyl chloride

Product 1

HCID 68749628N-[3-(4-chloro-3-methylphenyl)-5,7-dimethylpyrazolo[1,5-a]pyrimidin-2-yl]-2-(cyclopentyloxy)acetamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The product from Example 133C (1.0 mL of solution in CH2Cl2) was added to a stirring solution of the product from Example 47C (51 mg, 0.178 mmol) in pyridine (1.4 mL). The reaction mixture was stirred at room temperature for 2 hours, and then quenched by addition of MeOH (0.5 mL). After 30 min, concentrated NH4OH (0.2 mL) was added, and the mixture was stirred at room temperature for 12 hours, and then concentrated under vacuum. The residue was purified by flash chromatography (silica gel, eluted with hexanes-EtOAc, 70:30-0:100) to provide the title compound. 1H NMR (300 MHz, CD3OD) δ ppm 1.52-1.81 (m, 8H) 2.42 (s, 3H) 2.56 (s, 3H) 2.73 (d, J=1.0 Hz, 3H) 4.05-4.12 (m, 1H) 4.09 (s, 2H) 6.86-6.89 (q, J=1.0 Hz, 1H) 7.40 (d, J=8.5 Hz, 1H) 7.54 (dd, J=8.4, 1.9 Hz, 1H) 7.65 (d, J=1.9 Hz, 1H); MS (DCI/NH3) m/z 413/415 (M+H)+.

Workup

  1. customquenched by addition of MeOH (0.5 mL)
  2. waitAfter 30 min
  3. additionconcentrated NH4OH (0.2 mL) was added
  4. stirringthe mixture was stirred at room temperature for 12 hours
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by flash chromatography (silica gel, eluted with hexanes-EtOAc, 70:30-0:100)

Sources & evidence

ORD record
ord-9d01b86a77284d3ca2323975d881efb7
Source dataset
uspto-grants-2013_12
Patent number
US08609669B2

Reaction notes

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