Ammonium Chloride → 4-[3,4-Diamino-2-(cyclopropylmethoxy)phenyl]-6-methyl-1-[(4-methylphenyl)sulfonyl]-1,6-dihydro-7H-pyrrolo[2,3-c]pyridin-7-one

HRID 1056949ノート

反応式

HRID 1056949 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]3[CH:18]=[CH:17][N:16]([S:19]([C:22]4[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=4)(=[O:21])=[O:20])[C:10]=3[C:11](=[O:15])[N:12]([CH3:14])[CH:13]=2)=[C:4]([O:29][CH2:30][CH:31]2[CH2:33][CH2:32]2)[C:3]=1[N+:34]([O-])=O.[Cl-].[NH4+]>C(OCC)(=O)C.CO.ClCCl.[Zn]>[NH2:34][C:3]1[C:4]([O:29][CH2:30][CH:31]2[CH2:33][CH2:32]2)=[C:5]([C:8]2[C:9]3[CH:18]=[CH:17][N:16]([S:19]([C:22]4[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=4)(=[O:21])=[O:20])[C:10]=3[C:11](=[O:15])[N:12]([CH3:14])[CH:13]=2)[CH:6]=[CH:7][C:2]=1[NH2:1]

参加物

7

反応物 2

HCID 25517Ammonium ChlorideHCID 1180939284-(4-Amino-2-(cyclopropylmethoxy)-3-nitrophenyl)-6-methyl-l-tosyl-1H-pyrrolo[2,3-c]pyridin-7(6H)-one

生成物 1

HCID 1180939054-[3,4-Diamino-2-(cyclopropylmethoxy)phenyl]-6-methyl-1-[(4-methylphenyl)sulfonyl]-1,6-dihydro-7H-pyrrolo[2,3-c]pyridin-7-one

試薬・触媒・溶媒 4

HCID 23994Zinc触媒HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒2 回HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

A suspension of 4-[4-amino-2-(cyclopropylmethoxy)-3-nitrophenyl]-6-methyl-1-[(4-methylphenyl)sulfonyl]-1,6-dihydro-7H-pyrrolo[2,3-c]pyridin-7-one (0.119 g, 0.234 mmol) in ethyl acetate (1.2 mL) and methanol (1.2 mL) was treated with saturated aqueous ammonium chloride solution (0.274 mL, 4.09 mmol). The mixture was cooled to 0° C., treated with zinc (0.122 g, 1.87 mmol) in two portions over 5 min, stirred at RT for 30 min and heated at 55° C. for 1 h. The reaction mixture was diluted with dichloromethane, filtered through a Celite pad, and the solids were washed with dichloromethane. The filtrate was concentrated to give a residue. The residue was dissolved in dichloromethane (30 mL), washed with saturated sodium bicarbonate solution (20 mL), dried with sodium sulfate, filtered, and concentrated to give the desired product that was used without further purification. LCMS calculated for C25H27N4O4S (M+H)+: m/z=479.2. found: 479.1.

後処理

  1. temperatureheated at 55° C. for 1 h
  2. filtrationfiltered through a Celite pad
  3. washthe solids were washed with dichloromethane
  4. concentrationThe filtrate was concentrated
  5. customto give a residue
  6. washwashed with saturated sodium bicarbonate solution (20 mL)
  7. dry with materialdried with sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-8901c283508a4f469fa34184da9d6266
出典データセット
uspto-grants-2016_07
特許番号
US09399640B2

反応ノート

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