Sodium borohydride → HCID 178521626, compound

HRID 1028729Notes

Reaction equation

HRID 1028729 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]=1

Participants

3

Reactant 2

HCID 4311764Sodium borohydrideHCID 469372693-(8-Chloro-1-(2-phenylquinolin-7-yl)imidazo[1,5-a]pyrazin-3-yl)cyclobutanone

Product 1

HCID 178521626HCID 178521626, compound

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

  1. customThe reaction mixture was quenched by an addition of Na2SO4.10H2O
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe crude mixture was dissolved in DCM
  4. washwashed with water (3×15 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-eb667a9e97b34b7485b7d9edef511a32
Source dataset
uspto-grants-2014_05
Patent number
US08735405B2

Reaction notes

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