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Ammonium Chloride → N-[(1S)-2-amino-1-phenylethyl]-methyl-8-{[4-(4-methylpiperazin-1-yl)phenyl]amino}-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide

HRID 875135
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HRID 875135 반응식
[N:1]([CH2:4][C@@H:5]([NH:12][C:13]([C:15]1[C:19]2[CH2:20][CH2:21][C:22]3[CH:23]=[N:24][C:25]([NH:28][C:29]4[CH:34]=[CH:33][C:32]([N:35]5[CH2:40][CH2:39][N:38]([CH3:41])[CH2:37][CH2:36]5)=[CH:31][CH:30]=4)=[N:26][C:27]=3[C:18]=2[N:17]([CH3:42])[N:16]=1)=[O:14])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[N+]=[N-].[NH4+].[Cl-]>CO.O.[Fe]>[NH2:1][CH2:4][C@@H:5]([NH:12][C:13]([C:15]1[C:19]2[CH2:20][CH2:21][C:22]3[CH:23]=[N:24][C:25]([NH:28][C:29]4[CH:30]=[CH:31][C:32]([N:35]5[CH2:40][CH2:39][N:38]([CH3:41])[CH2:37][CH2:36]5)=[CH:33][CH:34]=4)=[N:26][C:27]=3[C:18]=2[N:17]([CH3:42])[N:16]=1)=[O:14])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 2

HCID 25517Ammonium ChlorideHCID 57531684N-[(1S)-2-azido-1-phenylethyl]-1-methyl-8-{[4-(4-methylpiperazin-1-yl)phenyl]amino}-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide

생성물 1

HCID 57531675N-[(1S)-2-amino-1-phenylethyl]-methyl-8-{[4-(4-methylpiperazin-1-yl)phenyl]amino}-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide수율 76.7%

시약·촉매·용매 3

HCID 23925Iron촉매
HCID 887Methanol용매
HCID 962Water용매

실험 절차

To a solution of 129 mg (0.228 mmol) of N-[(1S)-2-azido-1-phenylethyl]-1-methyl-8-{[4-(4-methylpiperazin-1-yl)phenyl]amino}-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide in 16 mL of methanol, 65 mg (1.2 mmol) of NH4Cl dissolved in 3.2 mL of water and 39 mg of iron (0.7 mmol) were added and the mixture refluxed overnight. The suspension was cooled to room temperature and filtered. After removal of methanol, solid Na2CO3 was added portionwise to the aqueous phase up to pH 10 and the product was then extracted with dichloromethane. Flash chromatography of the crude (eluant dichloromethane/methanol 95/5) yielded 94 mg of the title compound.

후처리

  1. temperaturethe mixture refluxed overnight
  2. filtrationfiltered
  3. customAfter removal of methanol, solid Na2CO3
  4. additionwas added portionwise to the aqueous phase up to pH 10
  5. extractionthe product was then extracted with dichloromethane

출처 및 근거

ORD 기록
ord-f96430332ef44b44a8ff498b8f6c6fff
출처 데이터셋
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08981089B2

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