Dimethylformamide → HCID 18464583, compound

HRID 2230672Notes

Reaction equation

HRID 2230672 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[NH:19][C:18]3[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=3[N:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:24][N:25](C)[CH:26]=[O:27].[H-].[Na+].CO.Cl[CH2:34]Cl>>[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[N:16]([N:25]([CH3:24])[C:26](=[O:27])[CH3:34])[C:17]3[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=3[N:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 184646551-t-butoxycarbonyl-4-(1H-benzimidazol-2-yl)[1,4]diazepaneHCID 21226129Dichloromethane methanol

Product 1

HCID 18464583HCID 18464583, compound

Conditions

Temperature
70 °C

Procedure

Combine 1-(t-butoxycarbonyl)-4-(1H-benzimidazol-2-yl)[1,4]diazepane (0.5 g, 1.6 mmol) and dimethylformamide (20 mL). Add sodium hydride (0.08 g, 3.2 mmol). After 12 hours, add N-methyl-1-chloroacetamide (0.34 g, 3.14 mmol). After 12 hours, add N-methyl-1-chloroacetamide (0.17 g, 1.6 mmol). After 12 hours, heat to 70° C. After 4 hours, cool to ambient temperature and partition the reaction mixture between water (10 mL) and dichloromethane (100 mL). Separate the layers, dry the organic layer over Na2SO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with 1.2% methanol/dichloromethane/0.5% saturated aqueous ammonia solution to give 1-(t-butoxycarbonyl)-4-(1-(N-methylacetamido)-1H-benzimidazol-2-yl)[1,4]diazepane: Rf=0.24 (silica gel, 1.8% methanol/dichloromethane/0.5% saturated aqueous ammonia solution).

Workup

  1. waitAfter 12 hours
  2. waitAfter 12 hours
  3. waitAfter 4 hours
  4. temperaturecool to ambient temperature
  5. custompartition the reaction mixture between water (10 mL) and dichloromethane (100 mL)
  6. customSeparate the layers
  7. dry with materialdry the organic layer over Na2SO4
  8. filtrationfilter
  9. customevaporate in vacuo
  10. customto give a residue

Sources & evidence

ORD record
ord-433f2c4fed254fffa247469840c915c8
Source dataset
uspto-grants-2002_07
Patent number
US06423704B1

Reaction notes

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