Ethyl Acetate → 6-Amino-4'-[3-(propane-2-sulfonylamino)-thiophen-2-yl]-biphenyl-2-carboxylic acid methyl ester

HRID 746783Notes

Reaction equation

HRID 746783 reaction equation
BrC1C=C(F)C(OC(=O)C(C)(C)C)=C(F)C=1C#N.[CH3:19][O:20][C:21]([C:23]1[C:24]([C:32]2[CH:37]=[CH:36][C:35]([C:38]3[S:39][CH:40]=[CH:41][C:42]=3[NH:43][S:44]([CH:47]([CH3:49])[CH3:48])(=[O:46])=[O:45])=[CH:34][CH:33]=2)=[C:25]([N+:29]([O-])=O)[CH:26]=[CH:27][CH:28]=1)=[O:22].CCOC(C)=O>CCO>[CH3:19][O:20][C:21]([C:23]1[C:24]([C:32]2[CH:33]=[CH:34][C:35]([C:38]3[S:39][CH:40]=[CH:41][C:42]=3[NH:43][S:44]([CH:47]([CH3:49])[CH3:48])(=[O:46])=[O:45])=[CH:36][CH:37]=2)=[C:25]([NH2:29])[CH:26]=[CH:27][CH:28]=1)=[O:22]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 692549916-Nitro-4'-[3-(propane-2-sulfonylamino)-thiophen-2-yl]-biphenyl-2-carboxylic acid methyl esterHCID 866131722,2-Dimethyl-propionic acid 4-bromo-3-cyano-2,6-difluoro-phenyl ester

Product 1

HCID 692534626-Amino-4'-[3-(propane-2-sulfonylamino)-thiophen-2-yl]-biphenyl-2-carboxylic acid methyl esterYield 89.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Add SnCl2 2 H2O (470 mg, 2.8 mmol) to a solution of 6-nitro-4′-[3-(propane-2-sulfonylamino)-thiophen-2-yl]-biphenyl-2-carboxylic acid methyl ester (250 mg, 0.54 mmol) in EtOH (5 mL). Heat the reaction at 80° C. for 3 hours. Add 100 mL EtOAc and wash it with a saturated solution of NaHCO3, water and saturated aq. sodium chloride (50 mL). Dry over NaSO4, filter and evaporate to dryness to provide 6-amino-4′-[3-(propane-2-sulfonylamino)-thiophen-2-yl]-biphenyl-2-carboxylic acid methyl ester (208 mg). MS (m/e): 429.1(M−1).

Workup

  1. temperatureHeat
  2. customthe reaction at 80° C. for 3 hours
  3. washwash it with a saturated solution of NaHCO3, water and saturated aq. sodium chloride (50 mL)
  4. dry with materialDry over NaSO4
  5. filtrationfilter
  6. customevaporate to dryness

Sources & evidence

ORD record
ord-390161c4f29a454b807f6ca0bc5369ed
Source dataset
uspto-grants-2008_07
Patent number
US07393868B2

Reaction notes

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