3-Cyclopentylpropionyl chloride → HCID 68753487, compound

HRID 1912909Notes

Reaction equation

HRID 1912909 reaction equation
[C:1]([C:5]1[C:6]([NH2:14])=[N:7][N:8]2[CH:13]=[CH:12][CH:11]=[N:10][C:9]=12)([CH3:4])([CH3:3])[CH3:2].[CH:15]1([CH2:20][CH2:21][C:22](Cl)=[O:23])[CH2:19][CH2:18][CH2:17][CH2:16]1>N1C=CC=CC=1>[C:1]([C:5]1[C:6]([NH:14][C:22](=[O:23])[CH2:21][CH2:20][CH:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)=[N:7][N:8]2[CH:13]=[CH:12][CH:11]=[N:10][C:9]=12)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 660393-Cyclopentylpropionyl chlorideHCID 687554713-Tert-butylpyrazolo[1,5-a]pyrimidin-2-amine

Product 1

HCID 68753487HCID 68753487, compoundYield 77.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture from Example 105B (71.2 mg, 0.37 mmol) and 3-cyclopentylpropionyl chloride (94.4 mg, 0.59 mmol) in pyridine (2 mL) was stirred at ambient temperature for 5 h. The mixture was concentrated. Purification by reverse phase HPLC afforded 90.3 mg (77%) of the title compound. 1H NMR (300 MHz, DMSO-d6): δ ppm 1.04-1.15 (m, 2H), 1.44-1.81 (m, 18H), 2.27-2.31 (m, 2H), 6.99 (dd, J=7.0, 3.9 Hz, 1H), 8.48 (dd, J=3.9, 1.9 Hz, 1H), 8.92 (dd, J=7.1, 1.7 Hz, 1H), 9.67 (br s, 1H); MS (DCI) m/z 315 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated
  2. customPurification by reverse phase HPLC

Sources & evidence

ORD record
ord-aefb89adad3f4de6ae494a92b669010b
Source dataset
uspto-grants-2013_12
Patent number
US08609669B2

Reaction notes

Loading…