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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
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HRID 1776864 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 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

생성물 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-carboxamide수율 62.5%

시약·촉매·용매 2

HCID 23938Palladium촉매
HCID 887
Methanol
용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-33868d331dda41db85603ec503a19d2e
출처 데이터셋
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09265773B2

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