Methanol → 4-Amino-2-[2-[2-(thiophen-2-ylcarbonylamino)ethoxy]-4-methoxybenzoyl-amino]-N-(4-methoxyphenyl)benzamide

HRID 644266

Reaction equation

HRID 644266 reaction equation
CO[C:3]1[CH:4]=[C:5]([C:8]([NH:10][CH2:11][CH2:12][O:13][C:14]2[CH:42]=[CH:41][CH:40]=[CH:39][C:15]=2[C:16]([NH:18][C:19]2[CH:35]=[C:34]([N+:36]([O-])=O)[CH:33]=[CH:32][C:20]=2[C:21]([NH:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=2)=[O:22])=[O:17])=[O:9])[S:6][CH:7]=1.[BH4-].[Na+].[CH3:45][OH:46]>C1COCC1.O.O.O.O.C([O-])(=O)C.[Ni+2].C([O-])(=O)C>[NH2:36][C:34]1[CH:33]=[CH:32][C:20]([C:21]([NH:23][C:24]2[CH:25]=[CH:26][C:27]([O:30][CH3:31])=[CH:28][CH:29]=2)=[O:22])=[C:19]([NH:18][C:16](=[O:17])[C:15]2[CH:39]=[CH:40][C:41]([O:46][CH3:45])=[CH:42][C:14]=2[O:13][CH2:12][CH2:11][NH:10][C:8]([C:5]2[S:6][CH:7]=[CH:3][CH:4]=2)=[O:9])[CH:35]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 685339172-[2-[4-methoxy-2-(thiophen-2-ylcarbonylamino)ethoxy]benzoylamino]-N-(4-methoxyphenyl)-4-nitrobenzamide

Product 1

HCID 578608374-Amino-2-[2-[2-(thiophen-2-ylcarbonylamino)ethoxy]-4-methoxybenzoyl-amino]-N-(4-methoxyphenyl)benzamideYield 81%

Reagents, catalysts & solvents 2

HCID 62601Nickel acetate tetrahydrateCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

The 2-[2-[4-methoxy-2-(thiophen-2-ylcarbonylamino)ethoxy]benzoylamino]-N-(4-methoxyphenyl)-4-nitrobenzamide (258 mg, 0.44 mmol) was diluted with methanol (20 mL) and THF (20 mL). Nickel acetate tetrahydrate (220 mg, 0.88 mmol) was added and the mixture was cooled to 0° C. Sodium borohydride (72 mg, 1.90 mmol) was then added in portions. Vigorous bubbling occurred and the reaction turned black. After 15 minutes, the reaction was concentrated in vacuo. The crude residue was diluted with EtOAc (60 mL), water (20 mL), and concentrated ammonium hydroxide (10 mL). The resulting mixture was stirred for 5 minutes and then it was poured into a separatory funnel and the layers were separated. The organic layer was washed with water (20 mL) and brine (20 mL) and then dried over magnesium sulfate, filtered and concentrated to give the desired product (201 mg, 0.36 mmol, 81%) as a grey solid.

Workup

  1. customVigorous bubbling
  2. concentrationthe reaction was concentrated in vacuo
  3. additionThe crude residue was diluted with EtOAc (60 mL), water (20 mL), and concentrated ammonium hydroxide (10 mL)
  4. additionit was poured into a separatory funnel
  5. customthe layers were separated
  6. washThe organic layer was washed with water (20 mL) and brine (20 mL)
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-351fcb598d4441b48ce98eea169c3789
Source dataset
uspto-grants-2010_04
Patent number
US07700628B2

Linked notes

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