Water → HCID 67141937, compound

HRID 1445111Notes

Reaction equation

HRID 1445111 reaction equation
[BH4-].[Na+].[ClH:3].[CH2:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][CH2:6][N:5]1[C:14]1[N:15]=[C:16]([C:33](=[O:35])[CH3:34])[CH:17]=[C:18]2[C:22]([CH3:23])=[C:21]([CH3:24])[N:20]([CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[CH:27]=3)[C:19]=12.O>CO>[ClH:3].[CH2:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][CH2:6][N:5]1[C:14]1[N:15]=[C:16]([CH:33]([OH:35])[CH3:34])[CH:17]=[C:18]2[C:22]([CH3:23])=[C:21]([CH3:24])[N:20]([CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[CH:27]=3)[C:19]=12

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 67141968HCID 67141968, compound

Product 1

HCID 67141937HCID 67141937, compoundYield 30.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (5.3 mg, 0.14 mmol) was added at 0° C. to a solution of 1-[7-(3,4-dihydro-1H-isoquinolin-2-yl)-1-(3-fluorobenzyl)-2,3-dimethyl-1H-pyrrolo[2,3-c]pyridin-5-yl]-ethanone hydrochloride (20 mg, 0.05 mmol) prepared in Example 855 in anhydrous methanol (2 ml). The reaction mixture was stirred for 10 minutes at the same temperature. Water was added to the reaction mixture, which was then extracted with ethyl acetate. The organic layer was dried on anhydrous magnesium sulfate and then concentrated under reduced pressure. The resulting residue was purified with silica gel column chromatography (ethyl acetate/n-hexane=1/3, v/v). The resulting residue was dissolved in ethyl acetate, saturated with hydrochloric acid gas, and then filtered to give 7.1 mg of the titled compound as a white solid.

Workup

  1. extractionwas then extracted with ethyl acetate
  2. dry with materialThe organic layer was dried on anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified with silica gel column chromatography (ethyl acetate/n-hexane=1/3
  5. dissolutionThe resulting residue was dissolved in ethyl acetate, saturated with hydrochloric acid gas
  6. filtrationfiltered

Sources & evidence

ORD record
ord-74e9d6d669284e0a8e161659e74c6e88
Source dataset
uspto-grants-2010_02
Patent number
US07662832B2

Reaction notes

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