Dimethylformamide → N-(4-Bromophenyl)-5-(3-{2,6-dichloro-3-[(2,2-dimethyl-propionylamino)-methyl]-phenyl}-thioureido)-2-fluoro-4-methylamino-benzamide

HRID 410104Notes

Reaction equation

HRID 410104 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:20])[C:10]2[CH:15]=[C:14]([NH2:16])[C:13]([NH:17][CH3:18])=[CH:12][C:11]=2[F:19])=[CH:4][CH:3]=1.[Cl:21][C:22]1[C:35]([N:36]=[C:37]=[S:38])=[C:34]([Cl:39])[CH:33]=[CH:32][C:23]=1[CH2:24][NH:25][C:26](=[O:31])[C:27]([CH3:30])([CH3:29])[CH3:28].CN(C=O)C>O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:20])[C:10]2[CH:15]=[C:14]([NH:16][C:37]([NH:36][C:35]3[C:34]([Cl:39])=[CH:33][CH:32]=[C:23]([CH2:24][NH:25][C:26](=[O:31])[C:27]([CH3:28])([CH3:30])[CH3:29])[C:22]=3[Cl:21])=[S:38])[C:13]([NH:17][CH3:18])=[CH:12][C:11]=2[F:19])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 56840192N-[(2,4-dichloro-3-isothiocyanatophenyl)methyl]-2,2-dimethylpropanamideHCID 68052072N-(4-bromophenyl)-2-fluoro-4-methylamino-5-amino-benzamide

Product 1

HCID 86669631N-(4-Bromophenyl)-5-(3-{2,6-dichloro-3-[(2,2-dimethyl-propionylamino)-methyl]-phenyl}-thioureido)-2-fluoro-4-methylamino-benzamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of N-(4-bromophenyl)-2-fluoro-4-methylamino-5-amino-benzamide (220 mg, 0.543 mmol), N-(2,4-Dichloro-3-isothiocyanato-benzyl)-2,2-dimethyl-propionamide (0.172 mg, 0.543 mmol) and DMF (5 mL) is stirred for 3 d, diluted with water, and extracted with EtOAc. The organic phase is washed with water, dried with Na2SO4 and concentrated to give the crude product.

Workup

  1. extractionextracted with EtOAc
  2. washThe organic phase is washed with water
  3. dry with materialdried with Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-7d2936f4364f4ec29166e8b274055324
Source dataset
uspto-grants-2014_06
Patent number
US08759537B2

Reaction notes

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