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

HRID 644266

反応式

HRID 644266 の反応式
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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 62601Nickel acetate tetrahydrate触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-351fcb598d4441b48ce98eea169c3789
出典データセット
uspto-grants-2010_04
特許番号
US07700628B2

関連ノート

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