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5-(6-(azidomethyl)-11-fluoro-6H-pyrido[2',3':5,6][1,3]oxazino[3,4-a]indol-2-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide → 5-(6-(aminomethyl)-11-fluoro-6H-pyrido[2',3':5,6][1,3]oxazino[3,4-a]indol-2-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide

HRID 1776864
ノート
印刷プレビュー

反応式

HRID 1776864 の反応式
[N:1]([CH2:4][CH:5]1[N:10]2[C:11]3[CH:12]=[CH:13][CH:14]=[C:15]([F:18])[C:16]=3[CH:17]=[C:9]2[C:8]2[N:19]=[C:20]([C:23]3[C:24]([N:43]([CH3:48])[S:44]([CH3:47])(=[O:46])=[O:45])=[CH:25][C:26]4[O:30][C:29]([C:31]5[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=5)=[C:28]([C:38]([NH:40][CH3:41])=[O:39])[C:27]=4[CH:42]=3)[CH:21]=[CH:22][C:7]=2[O:6]1)=[N+]=[N-]>CO.[Pd]>[NH2:1][CH2:4][CH:5]1[N:10]2[C:11]3[CH:12]=[CH:13][CH:14]=[C:15]([F:18])[C:16]=3[CH:17]=[C:9]2[C:8]2[N:19]=[C:20]([C:23]3[C:24]([N:43]([CH3:48])[S:44]([CH3:47])(=[O:45])=[O:46])=[CH:25][C:26]4[O:30][C:29]([C:31]5[CH:32]=[CH:33][C:34]([F:37])=[CH:35][CH:36]=5)=[C:28]([C:38]([NH:40][CH3:41])=[O:39])[C:27]=4[CH:42]=3)[CH:21]=[CH:22][C:7]=2[O:6]1
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 1

HCID 867282675-(6-(azidomethyl)-11-fluoro-6H-pyrido[2',3':5,6][1,3]oxazino[3,4-a]indol-2-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide

生成物 1

HCID 867282695-(6-(aminomethyl)-11-fluoro-6H-pyrido[2',3':5,6][1,3]oxazino[3,4-a]indol-2-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide収率 62.5%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒
HCID 887
Methanol
溶媒

実験手順

To a solution of 5-(6-(azidomethyl)-11-fluoro-6H-pyrido[2′,3′:5,6][1,3]oxazino[3,4-a]indol-2-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (2.8 g, 4.1 mmol) in MeOH (25 mL) at room temperature, 5% wet Pd/C (300 mg) was added and stirred under hydrogen atmosphere (30 psi) overnight. The reaction mixture was filtered. The filtrate was concentrated and the resulting residue was purified using silica gel column chromatography (dichloromethane:MeOH=20:1) to provide racemic 5-(6-(aminomethyl)-11-fluoro-6H-pyrido[2′,3′:5,6][1,3]oxazino[3,4-a]indol-2-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (1.5 g, yield: 62.5%). And after SFC separation, Compound 114 and 115 were obtained. Column: Chiralpak AD-3 50*4.6 mm I.D., 3 um Mobile phase:60% ethanol (0.05% DEA) in CO2. Flow rate: 3 mL/min Wavelength: 220 nm. Compound 114: RT=0.605 min, Compound 115: RT=1.393 minutes.

後処理

  1. filtrationThe reaction mixture was filtered
  2. concentrationThe filtrate was concentrated
  3. customthe resulting residue was purified

出典と根拠

ORDレコード
ord-33868d331dda41db85603ec503a19d2e
出典データセット
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09265773B2

反応ノート

読み込み中…

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