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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 44628
ノート
印刷プレビュー

反応式

HRID 44628 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 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

生成物 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-carboxamide収率 76.7%

試薬・触媒・溶媒 3

HCID 23925Iron触媒
HCID 887Methanol溶媒
HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-6f2ee9b1944b4353ae3aa0b18f2cd8bf
出典データセット
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08541429B2

反応ノート

読み込み中…

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