2-Methyl-1-(piperidin-4-yl)propan-1-ol → HCID 67063892, compound
Reaction equation
Cl[C:2]1[N:7]2[N:8]=[C:9](C)[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]([CH3:35])[CH:27]([CH:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1)[OH:28]>O1CCOCC1.CS(C)=O.CO>[OH:28][CH:27]([CH:29]1[CH2:30][CH2:31][N:32]([C:2]2[N:7]3[N:8]=[CH:9][CH:10]=[C:6]3[N:5]=[C:4]([NH:12][C:13](=[O:24])[C:14]3[CH:15]=[CH:16][C:17]([C:20]([OH:23])([CH3:21])[CH3:22])=[CH:18][CH:19]=3)[CH:3]=2)[CH2:33][CH2:34]1)[CH:26]([CH3:35])[CH3:25]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, 200 mg, 0.604 mmol) and 2-methyl-1-(piperidin-4-yl)propan-1-ol (142 mg, 0.604 mmol) in Dioxane (6 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, 5-95% (MeCN/H2O gradient+0.01% TFA). Lyophilization of the combined fractions gave the titled compound as a yellow solid (59 mg, 23%). 1H NMR (METHANOL-d4) δ: 7.99 (d, J=2.3 Hz, 1H), 7.92-7.97 (m, 2H), 7.61-7.69 (m, 2H), 7.39 (s, 1H), 6.32 (d, J=2.5 Hz, 1H), 4.55 (d, J=12.4 Hz, 2H), 2.93-3.14 (m, 3H), 2.02 (d, J=1.0 Hz, 1H), 1.58-1.89 (m, 5H), 1.57 (s, 6H), 0.96 (dd, 6H). ESI-MS: m/z 452.0 (M+H)+.
Workup
- customwas then purified by preparatory HPLC, 5-95% (MeCN/H2O gradient+0.01% TFA)
Sources & evidence
- ORD record
- ord-2dba8458388f48e0a4876f1b96506165
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08921358B2
Reaction notes
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