Diisopropylethylamine → HCID 178435850, compound

HRID 642888Notes

Reaction equation

HRID 642888 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[NH:13][C:12]3[C:14]([N:18]4[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]4)=[CH:15][CH:16]=[CH:17][C:11]=3[N:10]=2)=[CH:5][CH:4]=1)[CH3:2].Br[CH2:25][C:26]1[CH:31]=[CH:30][C:29]([F:32])=[C:28]([N+:33]([O-:35])=[O:34])[CH:27]=1.CCN(C(C)C)C(C)C>CN(C=O)C>[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[NH:13][C:12]3[C:14]([N:18]4[CH2:19][CH2:20][N:21]([CH2:25][C:26]5[CH:31]=[CH:30][C:29]([F:32])=[C:28]([N+:33]([O-:35])=[O:34])[CH:27]=5)[CH2:22][CH2:23]4)=[CH:15][CH:16]=[CH:17][C:11]=3[N:10]=2)=[CH:5][CH:4]=1)[CH3:2]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 108682084-Fluoro-3-nitrobenzyl bromideHCID 178435849HCID 178435849, compound

Product 1

HCID 178435850HCID 178435850, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(4-Ethyl-phenyl)-7-piperazin-1-yl-1H-benzoimidazole (200 mg, 0.65 mmol) and 4-bromomethyl-1-fluoro-2-nitro-benzene (152 mg, 0.65 mmol) were stirred together with DIEA (83 mg, 0.6.5 mmol) in DMF (4 ml) at room temperature. After 1 h, the reaction is complete and it was purified by HPLC Method E to yield the title product (100 mg (34%), 0.22 mmol). 1H NMR (DMSO-d6): δ=12.71 (s, 1H), 8.15 (m, 1H), 8.04 (d, J=8.2 Hz, 2H), 7.83 (m, 1H), 7.59 (m, 1H), 7.34 (d, J=8.2 Hz, 2H), 7.08 (m, 2H), 6.52 (dd, J=6.64, 1.94 Hz, 1H), 3.69 (s, 2H), 3.65 (bs, 4H), 2.75 (bs, 6H), 1.32 (t, J=7.6 Hz, 3H). Calculated mass=457.43, [M+H]+=458.

Workup

  1. customit was purified by HPLC Method E

Sources & evidence

ORD record
ord-7b3194b0a2424a4db75faa200df96090
Source dataset
uspto-grants-2010_04
Patent number
US07696210B2

Reaction notes

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