Sodium hydride → [4-(6-Carbamoylpyridin-3-yloxy)benzyl]phenethylcarbamic acid tert-butyl ester

HRID 130815

反応式

[C:1]([O:5][C:6](=[O:24])[N:7]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=1)[CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].F[C:28]1[CH:29]=[CH:30][C:31]([C:34]([NH2:36])=[O:35])=[N:32][CH:33]=1>CN(C=O)C>[C:1]([O:5][C:6](=[O:24])[N:7]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][C:28]2[CH:33]=[N:32][C:31]([C:34](=[O:35])[NH2:36])=[CH:30][CH:29]=2)=[CH:19][CH:18]=1)[CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([CH3:4])([CH3:2])[CH3:3]

参加物

反応条件

温度: 80 °C

実験手順

Dissolve (4-hydroxybenzyl)phenethylcarbamic acid tert-butyl ester (0.0915 g, 0.279 mol) in DMF (0.090 mL). Add NaH (80% in mineral oil) (0.0092 g, 0.307 mmol). Stir for 30 minutes before adding 5-fluoropyridine-2-carboxamide (0.0391 g, 0.279 mmol). Heat at 80° C. for 3 days. Load the reaction mixture directly onto a flash 40 column and elute with 35% ethyl acetate, 3% 2.0 M NH3 in methanol and 62% hexanes to give the title compound (0.103 g, 82.4%): MS ES+ 448.5 (M+H)+, base peak ES+ 392.3 (M+2H—C(CH3)3); HPLC [YMC-Pack Pro C-18 (150×4.6 mm, S-5 microm), acetonitrile in water containing 0.01% concentrated HCl at 1.0 mL/min, 5-95% over 19 min, 95% over 19.01-25 min], tR=19.5 min, 100% purity.

後処理

washLoad the reaction mixture directly onto a flash 40 column and elute with 35% ethyl acetate, 3% 2.0 M NH3 in methanol and 62% hexanes

出典と根拠

ORDレコード: ord-f493900e672c4040a954cc07924ce506
出典データセット: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US07381719B2

反応式

参加物

反応物 3

生成物 1

試薬・触媒・溶媒 1

反応条件

実験手順

後処理

出典と根拠

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