Hydrochloric Acid → N-(3-Chloro-4-fluoro-phenyl)-2-(2,6-dichloro-3-aminomethyl-phenylamino)-6-(2,2-difluoroethoxy)-1-methyl-1H-benzimidazole-5-carboxylic acid amide

HRID 410120Notes

Reaction equation

HRID 410120 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([C:12]2[C:39]([O:40][CH2:41][CH:42]([F:44])[F:43])=[CH:38][C:15]3[N:16]([CH3:37])[C:17]([NH:19][C:20]4[C:25]([Cl:26])=[CH:24][CH:23]=[C:22]([CH2:27][NH:28]C(OC(C)(C)C)=O)[C:21]=4[Cl:36])=[N:18][C:14]=3[CH:13]=2)=[O:11])[CH:5]=[CH:6][C:7]=1[F:8].Cl>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([C:12]2[C:39]([O:40][CH2:41][CH:42]([F:43])[F:44])=[CH:38][C:15]3[N:16]([CH3:37])[C:17]([NH:19][C:20]4[C:25]([Cl:26])=[CH:24][CH:23]=[C:22]([CH2:27][NH2:28])[C:21]=4[Cl:36])=[N:18][C:14]=3[CH:13]=2)=[O:11])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 56840392N-(3-chloro-4-fluoro-phenyl)-2-{2,6-dichloro-3-[(tert-butoxy-carbonylamino)-methyl]phenylamino}-6-(2,2-difluoroethoxy)-1-methyl-1H-benzimidazole-5-carboxylic acid amide

Product 1

HCID 86669639N-(3-Chloro-4-fluoro-phenyl)-2-(2,6-dichloro-3-aminomethyl-phenylamino)-6-(2,2-difluoroethoxy)-1-methyl-1H-benzimidazole-5-carboxylic acid amide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A mixture of N-(3-chloro-4-fluoro-phenyl)-2-{2,6-dichloro-3-[(tert-butoxy-carbonylamino)-methyl]phenylamino}-6-(2,2-difluoroethoxy)-1-methyl-1H-benzimidazole-5-carboxylic acid amide (4.0 g, 5.9 mmol, prepared in analogy to example 75 from N-(3-chloro-4-fluorophenyl)-2-(2,2-difluoroethoxy)-4-methylamino-5-amino-benzamide with building block B), 4 M HCl in dioxane (50 mL) and dioxane (200 mL) is stirred for 2 h. The precipitate is filtered off, washed with water and diluted with 10 mL conc. aq. NH3. The mixture is extracted with EtOAc, the organic phase is dried with Na2SO4 and concentrated.

Workup

  1. filtrationThe precipitate is filtered off
  2. washwashed with water
  3. additiondiluted with 10 mL conc. aq. NH3
  4. extractionThe mixture is extracted with EtOAc
  5. dry with materialthe organic phase is dried with Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-bac7058a157a4625a581e78e28f76c3d
Source dataset
uspto-grants-2014_06
Patent number
US08759537B2

Reaction notes

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