(2R)-2-(Methoxymethyl)pyrrolidine → HCID 67064477, 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][O:25][CH2:26][C@H:27]1[CH2:31][CH2:30][CH2:29][NH:28]1>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:28]3[CH2:29][CH2:30][CH2:31][C@@H:27]3[CH2:26][O:25][CH3:24])[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
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 (R)-2-(methoxymethyl)pyrrolidine (35 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 (44 mg, 72%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.46 (s, 6 H) 1.90-2.18 (m, 4 H) 3.24 (s, 3 H) 3.37 (dd, J=9.47, 7.20 Hz, 1 H) 3.54 (dd, J=9.73, 3.66 Hz, 1 H) 3.68-3.79 (m, 1 H) 3.83-3.98 (m, 1 H) 5.25 (br. s., 1 H) 6.28 (d, J=2.27 Hz, 1 H) 7.06 (s, 1 H) 7.61 (d, J=8.59 Hz, 2 H) 7.98 (d, J=8.59 Hz, 2 H) 8.04 (d, J=2.02 Hz, 1 H) 10.81 (s, 1 H). ESI-MS: m/z 410.3 (M+H)+.
Workup
- customwas then purified by preparatory HPLC, 20-45% (MeCN/H2O gradient+0.01% TFA)
Sources & evidence
- ORD record
- ord-5becce52ea714c06886938683a79d231
- Source dataset
- uspto-grants-2013_06
- Patent number
- US08461163B2
Reaction notes
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