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

HRID 644266

반응식

HRID 644266 반응식
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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 62601Nickel acetate tetrahydrate촉매HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-351fcb598d4441b48ce98eea169c3789
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07700628B2

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