Dimethylformamide → HCID 68432271, compound

HRID 1867450Notes

Reaction equation

HRID 1867450 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](/[CH:9]=[CH:10]/[C:11]([N:13]2[CH2:19][CH2:18][C:17](=[O:20])[NH:16][CH2:15][CH2:14]2)=[O:12])[CH:5]=[CH:6][C:7]=1[Cl:8].C[CH2:22][CH:23](Br)[CH2:24][CH2:25][CH2:26][Br:27].[H-].[Na+].[OH:31]S([O-])(=O)=O.[K+].CN([CH:40]=[O:41])C>>[CH3:40][O:41][C:22](=[O:31])[CH:23]([N:16]1[C:17](=[O:20])[CH2:18][CH2:19][N:13]([C:11](=[O:12])/[CH:10]=[CH:9]/[C:4]2[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=2)[CH2:14][CH2:15]1)[CH2:24][CH2:25][CH2:26][Br:27]

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 24758Sodium hydride2×HCID 516920Potassium bisulfateHCID 125758201,4-Dibromohexane2×HCID 620449211-[(E)-3-(3,4-Dichloro-phenyl)-acryloyl]-[1,4]diazepan-5-one2×

Product 1

HCID 68432271HCID 68432271, compoundYield 48%

Procedure

A solution of 0.501 g (1.60 mmol) of 1-[(E)-3-(3,4-dichloro-phenyl)-acryloyl]-[1,4]diazepan-5-one (intermediate 1A) and 0.447 g (1.60 mmol) of methyl 2,5-dibromopentane in 7 ml of DMF was treated at 0° C. with 0.077 g (1.76 mmol) of NaH (55% in oil). The reaction was stirred for 20 h at RT, cooled (0° C.) and treated again with 0.224 g (0.80 mmol) of methyl 2,5-dibromopentane and 0.038 g (0.88 mmol) of NaH (55% in oil). After 1 h at 0° C. and 3 h at RT, the reaction was neutralized with cold aqueous 10% KHSO4 and extracted with Et2O (3×). The organic phases were washed with aqueous 10% KHSO4, aqueous 10% NaCl, dried over Na2SO4 evaporated and purified by flash silica gel column (CH2Cl2/Et2O 95:5 to 70:30) to yield 0.39 g (48%) of the title compound as white foam. MS: 505.1 (MH+, 1Br).

Workup

  1. temperaturecooled (0° C.)
  2. waitAfter 1 h at 0° C.
  3. custom3 h
  4. customat RT
  5. extractionextracted with Et2O (3×)
  6. washThe organic phases were washed with aqueous 10% KHSO4, aqueous 10% NaCl
  7. dry with materialdried over Na2SO4
  8. customevaporated
  9. custompurified by flash silica gel column (CH2Cl2/Et2O 95:5 to 70:30)

Sources & evidence

ORD record
ord-5a6795d4db994ad690559614af294e09
Source dataset
uspto-grants-2009_12
Patent number
US07632829B2

Reaction notes

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