Ethyl Acetate → HCID 57785923, compound

HRID 1399242Notes

Reaction equation

HRID 1399242 reaction equation
CS(O[CH:6]1[CH2:15][N:14]2[C:10](=[N:11][C:12]3[CH:19]=[CH:18][CH:17]=[C:16]([N:20]([CH2:23][CH3:24])[CH2:21][CH3:22])[C:13]=32)[N:9]([C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][C:26]=2[Cl:32])[CH2:8][CH2:7]1)(=O)=O.[N-:33]=[N+:34]=[N-:35].[Na+].C(OCC)(=O)C>CN(C)C=O>[N:33]([CH:6]1[CH2:15][N:14]2[C:10](=[N:11][C:12]3[C:13]2=[C:16]([N:20]([CH2:23][CH3:24])[CH2:21][CH3:22])[CH:17]=[CH:18][CH:19]=3)[N:9]([C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][C:26]=2[Cl:32])[CH2:8][CH2:7]1)=[N+:34]=[N-:35].[Cl:32][C:26]1[CH:27]=[C:28]([Cl:31])[CH:29]=[CH:30][C:25]=1[N:9]1[C:10]2=[N:11][C:12]3[C:13](=[C:16]([N:20]([CH2:23][CH3:24])[CH2:21][CH3:22])[CH:17]=[CH:18][CH:19]=3)[N:14]2[CH:15]=[CH:6][CH2:7][CH2:8]1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 33557Sodium AzideHCID 57786380HCID 57786380, compound

Product 2

HCID 57785923HCID 57785923, compoundYield 75%HCID 57786221HCID 57786221, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1-(2,4-dichlorophenyl)-7-(diethylamino)-2,3,4,5-tetrahydro-1H-[1,3]diazepino[1,2-a]benzimidazol-4-yl methanesulfonate (144 mg, 0.289 mmol) and sodium azide (56.4 mg, 0.868 mmol) in N,N-dimethylformamide (1.4 mL) was stirred at 100° C. for 3 hr. Ethyl acetate was added, and the resultant mixture was washed with water and brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with a 10-30% ethyl acetate/n-hexane gradient mixture to give 4-azido-1-(2,4-dichlorophenyl)-N,N-diethyl-2,3,4,5-tetrahydro-1H-[1,3]diazepino[1,2-a]benzimidazol-7-amine as a colorless solid (96.6 mg, 0.217 mmol, 75%) and 1-(2,4-dichlorophenyl)-N,N-diethyl-2,3-dihydro-1H-[1,3]diazepino[1,2-a]benzimidazol-7-amine (21.4 mg, 00532 mmol, 18%).

Workup

  1. washthe resultant mixture was washed with water and brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash column chromatography on silica gel eluting with a 10-30% ethyl acetate/n-hexane gradient mixture

Sources & evidence

ORD record
ord-5fb2acef02db4ab49b63a09c7b77a0c2
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

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