Benzaldehyde → HCID 22185374, compound

HRID 1795146Notes

Reaction equation

HRID 1795146 reaction equation
[NH2:1][CH2:2][C:3]([C:6]1[NH:7][C:8]([C:19]2[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=2)=[C:9]([C:11]2[CH:12]=[CH:13][C:14]([Cl:18])=[C:15]([OH:17])[CH:16]=2)[N:10]=1)([CH3:5])[CH3:4].[CH:25](=O)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CO.C(OCC)(=O)C.C(=O)([O-])O.[Na+]>[CH2:25]([NH:1][CH2:2][C:3]([C:6]1[NH:7][C:8]([C:19]2[CH:20]=[CH:21][N:22]=[CH:23][CH:24]=2)=[C:9]([C:11]2[CH:12]=[CH:13][C:14]([Cl:18])=[C:15]([OH:17])[CH:16]=2)[N:10]=1)([CH3:5])[CH3:4])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

7

Reactant 3

HCID 240BenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 22185475HCID 22185475, compound

Product 1

HCID 22185374HCID 22185374, compoundYield 17%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of Example 3 (103 mg, 0.3 mmol) and benzaldehyde (30.7 mg, 0.3 mmol) in methanol (1 ml) was stirred at room temperature for 30 min. Sodium triacetoxyborohydride (76.3 mg, 0.36 mmol) was then added and the mixture stirred at room temperature for 3 hours before being diluted with ethyl acetate and sodium hydrogen carbonate solution. The aqueous layer was separated and re-extracted with additional ethyl acetate. The combined organic layers was then washed with brine, dried over anhydrous magnesium sulphate, filtered and concentrated under reduced pressure. The residue was chromatographed on silica gel eluting with dichloromethane/methanol/0.880 ammonia solution (20:1:0.1) to give the title compound (22 mg, 17%) as a pale yellow solid; MS(ES+) m/e 433/435 [M+H]+.

Workup

  1. customThe aqueous layer was separated
  2. extractionre-extracted with additional ethyl acetate
  3. washThe combined organic layers was then washed with brine
  4. dry with materialdried over anhydrous magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was chromatographed on silica gel eluting with dichloromethane/methanol/0.880 ammonia solution (20:1:0.1)

Sources & evidence

ORD record
ord-394785735172437ea0da3fb452fbab5d
Source dataset
uspto-grants-2006_04
Patent number
US07026336B1

Reaction notes

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