Bis-(1H-imidazol-2-YL)-methanone → Tert-butyl (3-(3-(3-(imidazo[1,2-a]pyridine-3-carboxamido)-4-methylphenyl)-1,2,4-oxadiazol-5-yl)oxetan-3-yl)carbamate

HRID 405796

反応式

C(C1NC=CN=1)(C1NC=CN=1)=O.[C:13]([O:17][C:18]([NH:20][C:21]1([C:25]([OH:27])=O)[CH2:24][O:23][CH2:22]1)=[O:19])([CH3:16])([CH3:15])[CH3:14].O[N:29]=[C:30]([C:32]1[CH:33]=[CH:34][C:35]([CH3:50])=[C:36]([NH:38][C:39]([C:41]2[N:45]3[CH:46]=[CH:47][CH:48]=[CH:49][C:44]3=[N:43][CH:42]=2)=[O:40])[CH:37]=1)[NH2:31]>CN1C(=O)CCC1>[N:43]1[CH:42]=[C:41]([C:39]([NH:38][C:36]2[CH:37]=[C:32]([C:30]3[N:29]=[C:25]([C:21]4([NH:20][C:18](=[O:19])[O:17][C:13]([CH3:14])([CH3:15])[CH3:16])[CH2:22][O:23][CH2:24]4)[O:27][N:31]=3)[CH:33]=[CH:34][C:35]=2[CH3:50])=[O:40])[N:45]2[CH:46]=[CH:47][CH:48]=[CH:49][C:44]=12

参加物

反応条件

温度: 125 °C

実験手順

Carbonyl diimidazole (CDI) (162.2 mg, 1.0 mmol) was added to a stirred solution of 3-((tert-butoxycarbonyl)amino)oxetane-3-carboxylic acid (45) (217.1 mg, 1.0 mmol)) in NMP (1.0 mL). After 20 minutes, N-(5-(N′-hydroxycarbamimidoyl)-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide (9) (150.0 mg, 0.5 mmol) was added in one portion and the resulting solution was stirred for 1 hour before it was heated at 125° C. for 15 minutes in a microwave reactor. The reaction solution was subjected to standard aqueous work up to afford a residue which was purified by silica chromatography to yield tert-butyl (3-(3-(3-(imidazo[1,2-a]pyridine-3-carboxamido)-4-methylphenyl)-1,2,4-oxadiazol-5-yl)oxetan-3-yl)carbamate (46) (159 mg, 65% yield). MS m/z 491.2 (M+1)+.

後処理

customto afford a residue which
customwas purified by silica chromatography

出典と根拠

ORDレコード: ord-941553a6c04141069044538e7f524bb2
出典データセット: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US08754071B2

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

関連ノート