(3S)-(-)-3-(Dimethylamino)pyrrolidine → HCID 67064229, compound
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.[CH3:24][N:25]([CH3:31])[C@H:26]1[CH2:30][CH2:29][NH:28][CH2:27]1>CN1C(=O)CCC1.CS(C)=O.CO>[CH3:24][N:25]([CH3:31])[C@H:26]1[CH2:30][CH2:29][N:28]([C:2]2[N:7]3[N:8]=[CH:9][CH:10]=[C:6]3[N:5]=[C:4]([NH:11][C:12](=[O:23])[C:13]3[CH:18]=[CH:17][C:16]([C:19]([OH:22])([CH3:21])[CH3:20])=[CH:15][CH:14]=3)[CH:3]=2)[CH2:27]1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 3
Procedure
A solution of N-(7-chloropyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide (2D, 50 mg, 0.151 mmol) and (S)—N,N-dimethylpyrrolidin-3-amine (34 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, 10-35% (MeCN/H2O gradient+0.01% TFA). Lyophilization of the combined fractions gave the titled compound as a white solid (60 mg, 97%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.45 (s, 6H) 2.20-2.37 (m, 1H) 2.61-2.71 (m, 1H) 2.90 (d, J=3.79 Hz, 6H) 3.79-3.91 (m, 1H) 4.02-4.19 (m, 2H) 4.35 (d, J=6.57 Hz, 2H) 6.26 (d, J=2.27 Hz, 1H) 7.15 (s, 1H) 7.60 (d, J=8.59 Hz, 2H) 7.99 (d, J=8.59 Hz, 2H) 8.04 (d, J=2.02 Hz, 1H) 9.87 (br. s., 1H) 10.77 (s, 1H). ESI-MS: m/z 409.3 (M+H)+.
Workup
- customwas then purified by preparatory HPLC, 10-35% (MeCN/H2O gradient+0.01% TFA)
Sources & evidence
- ORD record
- ord-780a2aa382b147feaa07ff58b2b905c8
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08921358B2
Reaction notes
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