Sodium borohydride → HCID 178521626, compound
Reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[C:5]2[N:6]([C:10]([CH:29]3[CH2:32][C:31](=[O:33])[CH2:30]3)=[N:11][C:12]=2[C:13]2[CH:22]=[C:21]3[C:16]([CH:17]=[CH:18][C:19]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[N:20]3)=[CH:15][CH:14]=2)[CH:7]=[CH:8][N:9]=1>>[Cl:3][C:4]1[C:5]2[N:6]([C:10]([C@@H:29]3[CH2:30][C@H:31]([OH:33])[CH2:32]3)=[N:11][C:12]=2[C:13]2[CH:22]=[C:21]3[C:16]([CH:17]=[CH:18][C:19]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[N:20]3)=[CH:15][CH:14]=2)[CH:7]=[CH:8][N:9]=1Participants
Procedure
An ethanolic suspension (20 mL) of 3-[8-chloro-1-(2-phenylquinolin-7-yl)imidazo[1,5-a]pyrazin-3-yl]cyclobutanone: (2.5 mmol) was charged with NaBH4 (2.5 mmol) at rt. The reaction mixture was stirred at rt for 30 min until the reaction solution turned clear. The reaction mixture was quenched by an addition of Na2SO4.10H2O and concentrated under reduced pressure. The crude mixture was dissolved in DCM, washed with water (3×15 mL), dried over Na2SO4, filtered and concentrated in vacuo to afford the title compound as a yellow solid. 1H NMR (400 MHz, CDCl3) δ 8.52 (s, 1H), 8.28 (d, J=8.0 Hz, 1H), 8.19 (d, J=8.0 Hz, 2H), 7.93-7.87 (m, 3H), 7.58-7.52 (m, 3H), 7.47-7.45 (m, 1H), 7.37 (d, J=5.2 Hz, 1H), 4.44 (b, 1H), 3.37 (p, J=8.0 Hz, 1H), 3.03-2.96 (m, 2H), 2.60-2.53 (m, 2H); MS (ES+): m/z 427 (100) [MH+].
Workup
- customThe reaction mixture was quenched by an addition of Na2SO4.10H2O
- concentrationconcentrated under reduced pressure
- dissolutionThe crude mixture was dissolved in DCM
- washwashed with water (3×15 mL)
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-daf4ae4d5cca476e9a90b6aa55bbe4d3
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08653268B2
Reaction notes
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