Acetic Acid → HCID 69156444, compound

HRID 750195Notes

Reaction equation

HRID 750195 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]([N:23]=[CH:24][CH2:25][CH2:26][CH2:27][CH3:28])[C:7](=[O:22])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][C:11]([Cl:21])=[CH:10][CH:9]=2)=[O:4].C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[CH3:1][O:2][C:3]([C:5]1[N:6]([NH:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[C:7](=[O:22])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][C:11]([Cl:21])=[CH:10][CH:9]=2)=[O:4]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 69155737HCID 69155737, compound

Product 1

HCID 69156444HCID 69156444, compoundYield 64.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 6-chloro-1-oxo-2-pentylidenamino-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic acid methyl ester (120 mg), acetic acid (76 μl) and methanol (5.0 ml) was added sodium cyano borohydride (80 mg) and the mixture was stirred at room temperature for 1 hr. The reaction mixture was concentrated under reduced pressure and saturated aqueous sodium hydrogen carbonate was added to the residue. The mixture was extracted with dichloromethane, and after drying, the organic layer was concentrated under reduced pressure. The residue was subjected to medium pressure preparative LC (hexane/ethyl acetate=9/1-1/1) to give the title compound (78 mg) as colorless crystals.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure and saturated aqueous sodium hydrogen carbonate
  2. additionwas added to the residue
  3. extractionThe mixture was extracted with dichloromethane
  4. customafter drying
  5. concentrationthe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7da8305c50b5467a89d705e1a8984560
Source dataset
uspto-grants-2008_07
Patent number
US07402595B2

Reaction notes

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