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 1056949노트

반응식

HRID 1056949 반응식
[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]

참가 물질

7

반응물 2

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

생성물 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

시약·촉매·용매 4

HCID 23994Zinc촉매HCID 887Methanol용매HCID 6344Dichloromethane용매2회HCID 8857Ethyl Acetate용매

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온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-8901c283508a4f469fa34184da9d6266
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09399640B2

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