1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (3,4-Difluorophenyl)-[1-(3,4-difluorophenyl)-1H-benzoimidazol-2-yl]amine

HRID 1176675Notes

Reaction equation

HRID 1176675 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:11]([NH2:16])=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:5]=[CH:6][C:7]=1[F:8].[F:17][C:18]1[CH:19]=[C:20]([N:25]=[C:26]=S)[CH:21]=[CH:22][C:23]=1[F:24].CN(C)CCCN=C=NCC>>[F:17][C:18]1[CH:19]=[C:20]([NH:25][C:26]2[N:9]([C:4]3[CH:5]=[CH:6][C:7]([F:8])=[C:2]([F:1])[CH:3]=3)[C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:16]=2)[CH:21]=[CH:22][C:23]=1[F:24]

Participants

4

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 27583313,4-Difluorophenyl IsothiocyanateHCID 29067155N-(3,4-difluorophenyl)benzene-1,2-diamine

Product 1

HCID 11559494(3,4-Difluorophenyl)-[1-(3,4-difluorophenyl)-1H-benzoimidazol-2-yl]amine

Procedure

The title compound was prepared by Procedure G from N-(3,4-difluorophenyl)-benzene-1,2-diamine (Scheme 5), 3,4-difluorophenyl isothiocyanate and, in the last step, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide. The reaction mixture was evaporated to dryness and the remaining crude product purified by preparative LCMS to give the title compound as the free base (solid, mp 115-117° C.). MS(ES+) m/z 358 ([M+1]+, 100).

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. customthe remaining crude product purified by preparative LCMS

Sources & evidence

ORD record
ord-bb76223aa0e449dd8574a14732146a5e
Source dataset
uspto-grants-2010_11
Patent number
US07842817B2

Reaction notes

Loading…