Pyrrolidine → HCID 66878313, compound

HRID 1409142Notes

Reaction equation

HRID 1409142 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[C:7]1[N:12]2[N:13]=[C:14]([CH3:16])[CH:15]=[C:11]2[N:10]=[C:9]([NH:17][C:18](=[O:30])[C:19]2[CH:24]=[CH:23][C:22]([C:25]([CH3:29])([CH3:28])[CH2:26][OH:27])=[CH:21][CH:20]=2)[CH:8]=1>CO>[OH:27][CH2:26][C:25]([C:22]1[CH:21]=[CH:20][C:19]([C:18]([NH:17][C:9]2[CH:8]=[C:7]([N:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)[N:12]3[N:13]=[C:14]([CH3:16])[CH:15]=[C:11]3[N:10]=2)=[O:30])=[CH:24][CH:23]=1)([CH3:29])[CH3:28]

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 86652263HCID 86652263, compound2×

Product 1

HCID 66878313HCID 66878313, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of N-(7-chloro-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)-4-(1-hydroxy-2-methylpropan-2-yl)benzamide (4G, 44 mg, 1.0 equivalent) and pyrrolidine (4.0 equivalents) in DMF (0.10 M with respect to 4G) was stirred at 80° C. for 1 h. After cooling, the mixture was diluted with methanol and purified by preparative LC-MS to afford the titled compound (76%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.26 (s, 6H), 1.85-2.07 (m, 4H), 2.33 (s, 3H), 3.47 (s, 2H), 3.96 (br. s., 4H), 6.13 (s, 1H), 6.75 (s, 1H), 7.53 (d, J=8.59 Hz, 2H), 7.97 (d, J=8.59 Hz, 2H), 10.89 (s, 1H). ESI-MS: m/z 394.3 (M+H)+.

Workup

  1. temperatureAfter cooling
  2. custompurified by preparative LC-MS

Sources & evidence

ORD record
ord-2c24c363411d47f082ca1d0a95a65af6
Source dataset
uspto-grants-2014_12
Patent number
US08921358B2

Reaction notes

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