1,3-Dibromopropane → HCID 44156377, compound

HRID 1628891Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[NH:14][C:13]2[C:15]([N:20]([CH2:23][CH3:24])[CH2:21][CH3:22])=[CH:16][CH:17]=[C:18]([F:19])[C:12]=2[N:11]=1.Br[CH2:26][CH2:27][CH2:28]Br.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:10]2=[N:11][C:12]3[C:13](=[C:15]([N:20]([CH2:23][CH3:24])[CH2:21][CH3:22])[CH:16]=[CH:17][C:18]=3[F:19])[N:14]2[CH2:28][CH2:27][CH2:26]1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of N2-(2,4-dichlorophenyl)-N7,N7-diethyl-4-fluoro-1H-benzimidazole-2,7-diamine (96.7 mg, 0.263 mmol), 1,3-dibromopropane (72.6 mg, 0.360 mmol) and potassium carbonate (113 mg, 0.819 mmol) in N,N-dimethylformamide (6 mL) was stirred at 80° C. for 3 hr. After ethyl acetate was added, the resultant mixture was washed with water and brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with ethyl acetate and preparative HPLC eluting with a 10-100% acetonitrile/water gradient mixture to give the title compound as a pale pink solid (38.2 mg, 0.0938 mmol, 36%).

Workup

washthe resultant mixture was washed with water and brine
dry with materialdried over anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified by column chromatography on silica gel eluting with ethyl acetate and preparative HPLC
washeluting with a 10-100% acetonitrile/water gradient mixture

Sources & evidence

ORD record: ord-95c0adec94054902a982a09d4f05a475
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785460B2

Reaction notes

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