Methanol → 2-(cyclopentyloxy)-N-(3-isopropylpyrazolo[1,5-a]pyrimidin-2-yl)acetamide

HRID 1912938Notes

Reaction equation

HRID 1912938 reaction equation
[CH:1]1([O: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].CO>N1C=CC=CC=1>[CH:1]1([O: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 3

HCID 887MethanolHCID 687533643-Isopropylpyrazolo[1,5-a]pyrimidin-2-amineHCID 866419172-(Cyclopentyloxy)acetyl chloride

Product 1

HCID 687528442-(cyclopentyloxy)-N-(3-isopropylpyrazolo[1,5-a]pyrimidin-2-yl)acetamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The product from Example 133C (1.5 mL of solution in CH2Cl2) was added to a solution of the product from Example 112C (86 mg, 0.49 mmol) in pyridine (1.0 mL) in a 4 mL vial. The reaction mixture was stirred at room temperature for 2 h. Methanol (0.5 mL) was added, and the solution was stirred for 30 minutes 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, CDCl3) δ ppm 1.45 (d, J=7.1 Hz, 6H) 1.57-1.69 (m, 2H) 1.70-1.87 (m, 6H) 3.24 (hept, J=7.1 Hz, 1H) 4.10-4.13 (m, 1H) 4.11-4.12 (m, 2H) 6.72 (dd, J=6.8, 4.1 Hz, 1H) 8.39 (dd, J=4.1, 1.7 Hz, 1H) 8.58 (dd, J=6.8, 1.7 Hz, 1H) 8.60 (s, 1H); MS (ESI) m/z 303 (M+H)+; Anal. Calculated for C16H22N4O2: C, 63.71; H, 7.44; N, 18.20. Found: C, 63.56; H, 7.33; N, 18.53.

Workup

  1. stirringthe solution was stirred for 30 minutes
  2. concentrationconcentrated under vacuum
  3. customThe residue was purified by flash chromatography (silica gel, eluted with hexanes-EtOAc, 70:30-0:100)

Sources & evidence

ORD record
ord-41605f1eead643b1a4f173359ce8d80b
Source dataset
uspto-grants-2013_12
Patent number
US08609669B2

Reaction notes

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