Piperazin-2-one → HCID 67064337, compound

HRID 1409157Notes

Reaction equation

HRID 1409157 reaction equation
Cl[C:2]1[N:7]2[N:8]=[CH:9][CH:10]=[C:6]2[N:5]=[C:4]([NH:11][C:12](=[O:23])[C:13]2[CH:18]=[CH:17][C:16]([C:19]([OH:22])([CH3:21])[CH3:20])=[CH:15][CH:14]=2)[CH:3]=1.[NH:24]1[CH2:29][CH2:28][NH:27][CH2:26][C:25]1=[O:30]>CN1C(=O)CCC1.CS(C)=O.CO>[OH:22][C:19]([C:16]1[CH:17]=[CH:18][C:13]([C:12]([NH:11][C:4]2[CH:3]=[C:2]([N:27]3[CH2:28][CH2:29][NH:24][C:25](=[O:30])[CH2:26]3)[N:7]3[N:8]=[CH:9][CH:10]=[C:6]3[N:5]=2)=[O:23])=[CH:14][CH:15]=1)([CH3:21])[CH3:20]

Participants

6

Reactant 2

HCID 231360Piperazin-2-oneHCID 86652272N-(7-chloropyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide

Product 1

HCID 67064337HCID 67064337, compoundYield 29%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideCatalystHCID 887MethanolSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of N-(7-chloropyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide (2D, 50 mg, 151 mmol) and piperazin-2-one (30 mg, 0.302 mmol) in NMP (0.950 mL) was stirred at 85° C. overnight. After cooling to room temperature, the mixture was diluted with a few drops of DMSO and methanol, and was then purified by preparatory HPLC, 20-45% (MeCN/H2O gradient+0.01% TFA). Lyophilization of the combined fractions gave the titled compound as a orange solid (17 mg, 29%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.46 (s, 6H) 3.43 (br. s., 2H) 4.08 (t, J=5.18 Hz, 2H) 4.27 (s, 2H) 6.38 (d, J=2.27 Hz, 1H) 7.41 (s, 1H) 7.60 (d, J=8.59 Hz, 2H) 8.00 (d, J=8.34 Hz, 2H) 8.11 (d, J=2.27 Hz, 1H) 8.23 (br. s., 1H) 10.93 (s, 1H). ESI-MS: m/z 395.2 (M+H)+.

Workup

  1. customwas then purified by preparatory HPLC, 20-45% (MeCN/H2O gradient+0.01% TFA)

Sources & evidence

ORD record
ord-7bc64273ce8547659372e521772bceba
Source dataset
uspto-grants-2014_12
Patent number
US08921358B2

Reaction notes

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