Acetaldehyde → HCID 68770466, compound

HRID 1399036Notes

Reaction equation

HRID 1399036 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:24])=[C:6]2[C:10]=1[N:9]=[C:8]1[N:11]([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=3[Cl:23])[CH2:12][CH2:13][CH2:14][CH2:15][N:7]21.[CH:25](=O)[CH3:26].[C:28](O[BH-](OC(=O)C)OC(=O)C)(=O)[CH3:29].[Na+]>CO.C(O)(=O)C>[Cl:1][C:2]1[C:3]([CH2:25][CH3:26])=[C:4]([CH2:28][CH3:29])[C:5]([NH2:24])=[C:6]2[C:10]=1[N:9]=[C:8]1[N:11]([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=3[Cl:23])[CH2:12][CH2:13][CH2:14][CH2:15][N:7]21

Participants

6

Reactant 3

HCID 177AcetaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 5778620410-Chloro-1-(2,4-dichlorophenyl)-2,3,4,5-tetrahydro-1H-[1,3]diazepino[1,2-a]benzimidazol-7-amine

Product 1

HCID 68770466HCID 68770466, compoundYield 24%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

To a solution of 10-chloro-1-(2,4-dichlorophenyl)-2,3,4,5-tetrahydro-1H-[1,3]diazepino[1,2-a]benzimidazol-7-amine (29 mg, 0.075 mmol) in methanol (5.0 mL) and acetic acid (1.0 mL) was added acetaldehyde (0.05 mL, 0.84 mmol) at 0° C. The resultant mixture was stirred at 0° C. for 30 min. To the reaction mixture was added sodium triacetoxyborohydride (173 mg, 0.84 mmol) at 0° C. After stirring at room temperature for 5 h, the mixture was con concentrated in vacuo, diluted with water, and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography on a silica gel eluting with a 10-50% ethyl acetate/n-hexane gradient mixture. The filtrate was concentrated in vacuo to give the title compound (8 mg, 0.018 mmol, 24%) as a white amorphous.

Workup

  1. concentrationthe mixture was con concentrated in vacuo
  2. additiondiluted with water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography on a silica gel eluting with a 10-50% ethyl acetate/n-hexane gradient mixture
  8. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-e886acef51734b0ea472f73128d9a515
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

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