Formic Acid → {4-[(E)-3-(3-Chloro-phenyl)-acryloyl]-7-oxo-[1,4]diazepan-1-yl}-acetaldehyde

HRID 1867357Notes

Reaction equation

HRID 1867357 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](/[CH:8]=[CH:9]/[C:10]([N:12]2[CH2:18][CH2:17][C:16](=[O:19])[N:15]([CH2:20][CH:21](OCC)[O:22]CC)[CH2:14][CH2:13]2)=[O:11])[CH:5]=[CH:6][CH:7]=1.C(O)=O.O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4](/[CH:8]=[CH:9]/[C:10]([N:12]2[CH2:18][CH2:17][C:16](=[O:19])[N:15]([CH2:20][CH:21]=[O:22])[CH2:14][CH2:13]2)=[O:11])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 284Formic AcidHCID 962WaterHCID 684321531-[(E)-3-(3-Chloro-phenyl)-acryloyl]-4-(2,2-diethoxy-ethyl)-[1,4]diazepan-5-one

Product 1

HCID 86615865{4-[(E)-3-(3-Chloro-phenyl)-acryloyl]-7-oxo-[1,4]diazepan-1-yl}-acetaldehydeYield 45.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 1.00 g (2.53 mmol) of 1-[(E)-3-(3-chloro-phenyl)-acryloyl]-4-(2,2-diethoxy-ethyl)-[1,4]diazepan-5-one in 10 ml of toluene was treated at RT with 5.22 ml formic acid and 1.5 ml water. The reaction was stirred for 1.5 h, evaporated and neutralized with aqueous saturated NaHCO3 and extracted with Et2O (3×). The organic phases were washed with aqueous 10% NaCl, dried over Na2SO4 evaporated and purified by flash silica gel column (EtOAc) to yield 0.37 g (45%) of the title compound as off-white foam. MS: 321.3 (MH+, Cl).

Workup

  1. customevaporated
  2. extractionextracted with Et2O (3×)
  3. washThe organic phases were washed with aqueous 10% NaCl
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. custompurified by flash silica gel column (EtOAc)

Sources & evidence

ORD record
ord-4c256c09299f4815929677b541b84b1c
Source dataset
uspto-grants-2009_12
Patent number
US07632829B2

Reaction notes

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