Acetic Acid → HCID 23156793, compound

HRID 1098291Notes

Reaction equation

HRID 1098291 reaction equation
[C:1](O)(=O)C.C([BH3-])#N.[Na+].[N:9]1([CH2:15][CH2:16][NH:17][C:18]2[CH:27]=[C:26]3[C:21]([CH:22]=[C:23]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[NH:24][C:25]3=[O:28])=[CH:20][CH:19]=2)[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1.C(=O)(O)[O-].[Na+]>CO>[CH3:1][N:17]([CH2:16][CH2:15][N:9]1[CH2:10][CH2:11][O:12][CH2:13][CH2:14]1)[C:18]1[CH:27]=[C:26]2[C:21]([CH:22]=[C:23]([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[NH:24][C:25]2=[O:28])=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 23156857HCID 23156857, compound

Product 1

HCID 23156793HCID 23156793, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.05 ml of acetic acid and 13.2 mg (0.168 mmol) of sodium cyanoborohydride were added to 0.5 ml of a methanol solution containing 14.7 mg (0.0241 mmol) of the 7-(2-morpholin-4-ylethylamino)-3-phenyl-2H-isoquinolin-1-one obtained in Example 15. The obtained mixture was stirred at a room temperature for 6 hours. Thereafter, a saturated sodium bicarbonate aqueous solution was added to the reaction solution, and the mixture was then extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and was then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (methylene chloride:methanol=20:1), so as to obtain 12.8 mg (84%) of 7-[methyl(2-morpholin-4-ylethyl)amino]-3-phenyl-2H-isoquinolin-1-one in the form of a yellow solid.

Workup

  1. extractionthe mixture was then extracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous sodium sulfate
  3. concentrationwas then concentrated under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (methylene chloride:methanol=20:1)

Sources & evidence

ORD record
ord-b950b3bb75fa4500a4bda77f23ec99c2
Source dataset
uspto-grants-2012_03
Patent number
US08143274B2

Reaction notes

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