Water → HCID 10295173, compound

HRID 1270183Notes

Reaction equation

HRID 1270183 reaction equation
[CH:1]1([C:7]2[CH:30]=[CH:29][C:10]([C:11]([N:13]3[C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=4[CH2:17][N:16]4[C:24]([CH:27]=[O:28])=[CH:25][CH:26]=[C:15]4[CH2:14]3)=[O:12])=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:31](Cl)(=O)C.[Sn](Cl)(Cl)(Cl)Cl.O>ClCCl>[CH:1]1([C:7]2[CH:30]=[CH:29][C:10]([C:11]([N:13]3[C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=4[CH2:17][N:16]4[C:24]([C:27](=[O:28])[CH3:31])=[CH:25][CH:26]=[C:15]4[CH2:14]3)=[O:12])=[CH:9][CH:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 24287Tin tetrachlorideHCID 18449084HCID 18449084, compound

Product 1

HCID 10295173HCID 10295173, compoundYield 33.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

10-(4-Cyclohexylbenzoyl)-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-carbaldehyde of Step A (3.7 g) dissolved in dichloromethane (75 mL) was treated with acetyl chloride (1.9 g) and tin (IV) chloride in dichloromethane (12.5 mL, 1N). After stirring overnight at room temperature, water was added. The organic solution was washed with saturated aqueous sodium bicarbonate, dried over anhydrous sodium sulfate and filtered through a short column of Magnesol® to provide the desired title compound as a pale yellow amorphous solid (1.3 g).

Workup

  1. washThe organic solution was washed with saturated aqueous sodium bicarbonate
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered through a short column of Magnesol®

Sources & evidence

ORD record
ord-bf7c971ce5534117a844a249562139c9
Source dataset
uspto-grants-2007_04
Patent number
US07202239B2

Reaction notes

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