HCID 57786103, compound → 10-Chloro-1-(2,4-dichlorophenyl)-2,3,4,5-tetrahydro-1H-[1,3]diazepino[1,2-a]benzimidazol-7-amine

HRID 1399035Notes

Reaction equation

HRID 1399035 reaction equation
[Cl:1][C:2]1[C:10]2[N:9]=[C:8]3[N:11]([C:16]4[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=4[Cl:23])[CH2:12][CH2:13][CH2:14][CH2:15][N:7]3[C:6]=2[C:5]([N+:24]([O-])=O)=[CH:4][CH:3]=1>[Pd].C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:24])=[C:6]2[C:10]=1[N:9]=[C:8]1[N:11]([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=3[Cl:23])[CH2:12][CH2:13][CH2:14][CH2:15][N:7]21

Participants

4

Reactant 1

HCID 57786103HCID 57786103, compound

Product 1

HCID 5778620410-Chloro-1-(2,4-dichlorophenyl)-2,3,4,5-tetrahydro-1H-[1,3]diazepino[1,2-a]benzimidazol-7-amineYield 65.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 10-chloro-1-(2,4-dichlorophenyl)-7-nitro-2,3,4,5-tetrahydro-1H-[1,3]diazepino[1,2-a]benzimidazole (53 mg, 0.129 mmol) and 10% palladium on carbon (6 mg) in acetic acid (5.0 mL) was stirred under hydrogen atmosphere at room temperature for 6 hr. The catalyst was removed by filtration and the filtrate was concentrated in vacuo. The residue was purified by flash chromatography on silica gel eluting with a 50-100% ethyl acetate/n-hexane gradient mixture. The filtrate was concentrated in vacuo to give the title compound (32 mg, 0.084 mmol, 65%) as an oil.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by flash chromatography on silica gel eluting with a 50-100% ethyl acetate/n-hexane gradient mixture
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-9d5d8dfb2c8348f78d6547eec30ade8d
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

Loading…