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反応

Pyridine → 2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide

HRID 1776872

印刷プレビュー

反応式

HRID 1776872 の反応式

NCC1N2C3C=CC=C(F)C=3C=C2C2N=C([C:21]3[C:22]([N:41]([CH3:46])[S:42]([CH3:45])(=[O:44])=[O:43])=[CH:23][C:24]4[O:28][C:27]([C:29]5[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=5)=[C:26]([C:36]([NH:38][CH3:39])=[O:37])[C:25]=4[CH:40]=3)C=CC=2O1.N1C=CC=CC=1.C(Cl)(=O)C>ClCCl.O>[F:35][C:32]1[CH:33]=[CH:34][C:29]([C:27]2[O:28][C:24]3[CH:23]=[C:22]([N:41]([CH3:46])[S:42]([CH3:45])(=[O:43])=[O:44])[CH:21]=[CH:40][C:25]=3[C:26]=2[C:36]([NH:38][CH3:39])=[O:37])=[CH:30][CH:31]=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 3

HCID 1049Pyridine

HCID 6367Acetyl chloride

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

生成物 1

HCID 694717192-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide収率 99.6%

試薬・触媒・溶媒 2

HCID 962

Water

溶媒

HCID 6344Dichloromethane溶媒

実験手順

A mixture of 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 (50 mg, 0.08 mmol), and pyridine (11 mg, 0.14 mmol) in dichloromethane (1 mL) was stirred at room temperature under N2 protection. Then acetyl chloride (11 mg, 0.14 mmol) was added and the solution was stirred at room temperature for 1.5 hours. Then the mixture was diluted with water (50 mL) and extracted with EtOAc (10 mL*3). The combined organic layer was washed with brine (30 mL), dried over Na2SO4 and concentrated in vacuo. The resulting residue was purified using prep-TLC (dichloromethane:MeOH=10:1) to provide 546-(acetamidomethyl)-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 (30 mg, yield: 56.3%). And after SFC separation, two enantiomers 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 129: RT=0.449 min, Compound 130: RT=1.264 minutes.

後処理

stirringthe solution was stirred at room temperature for 1.5 hours
extractionextracted with EtOAc (10 mL*3)
washThe combined organic layer was washed with brine (30 mL)
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo
customThe resulting residue was purified

出典と根拠

ORDレコード: ord-2b75bd44482a4d25ac486edf0a635f57
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

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