4-Methylpiperidine → HCID 67064663, compound

HRID 1256362Notes

Reaction equation

HRID 1256362 reaction equation
Cl[C:2]1[N:7]2[N:8]=[C:9]([CH3:11])[CH:10]=[C:6]2[N:5]=[C:4]([NH:12][C:13](=[O:24])[C:14]2[CH:19]=[CH:18][C:17]([C:20]([OH:23])([CH3:22])[CH3:21])=[CH:16][CH:15]=2)[CH:3]=1.[CH3:25][CH:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1>CN(C=O)C.CS(C)=O.CO>[OH:23][C:20]([C:17]1[CH:18]=[CH:19][C:14]([C:13]([NH:12][C:4]2[CH:3]=[C:2]([N:29]3[CH2:30][CH2:31][CH:26]([CH3:25])[CH2:27][CH2:28]3)[N:7]3[N:8]=[C:9]([CH3:11])[CH:10]=[C:6]3[N:5]=2)=[O:24])=[CH:15][CH:16]=1)([CH3:22])[CH3:21]

Participants

6

Reactant 2

HCID 693814-MethylpiperidineHCID 86652267N-(7-chloro-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide

Product 1

HCID 67064663HCID 67064663, compoundYield 87%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideCatalystHCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of N-(7-chloro-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide (2F, 86 mg, 0.25 mmol) and 4-methylpiperidine (77 mg, 0.75 mmol) in DMF (1.0 mL) was stirred at 100° C. for 2 h. After cooling to room temperature, the mixture was diluted with a few drops of DMSO and methanol, and was then purified by preparatory HPLC (45-45% MeCN/H2O gradient+0.01% TFA). Lyophilization of the combined fractions gave the titled compound as a white solid (88.6 mg, 87%). Melting point (154.0-158.0° C.). 1H NMR (DMSO-d6) δ: 10.85 (s, 1H), 7.99 (d, J=8.3 Hz, 2H), 7.60 (d, J=8.6 Hz, 2H), 7.29 (s, 1H), 6.16 (s, 1H), 4.46 (d, J=12.1 Hz, 2H), 2.98-3.10 (m, 2H), 2.37 (s, 3H), 1.78 (d, J=12.9 Hz, 2H), 1.61-1.74 (m, 1H), 1.46 (s, 6H), 1.28-1.39 (m, 2H), 0.98 (d, 3H); ESI-MS: m/z 408.3 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-81e49b2feb7142cbaaac7b2aa1b482ac
Source dataset
uspto-grants-2013_06
Patent number
US08461163B2

Reaction notes

Loading…