Methanesulfonyl chloride → (3-(3-(Imidazo[1,2-a]pyridine-3-carboxamido)-4-methylphenyl)-1,2,4-oxadiazol-5-yl)methyl methanesulfonate

HRID 570312

反応式

HRID 570312 の反応式
[OH:1][CH2:2][C:3]1[O:7][N:6]=[C:5]([C:8]2[CH:9]=[CH:10][C:11]([CH3:26])=[C:12]([NH:14][C:15]([C:17]3[N:21]4[CH:22]=[CH:23][CH:24]=[CH:25][C:20]4=[N:19][CH:18]=3)=[O:16])[CH:13]=2)[N:4]=1.CCN(C(C)C)C(C)C.[CH3:36][S:37](Cl)(=[O:39])=[O:38]>C(Cl)Cl>[CH3:36][S:37]([O:1][CH2:2][C:3]1[O:7][N:6]=[C:5]([C:8]2[CH:9]=[CH:10][C:11]([CH3:26])=[C:12]([NH:14][C:15]([C:17]3[N:21]4[CH:22]=[CH:23][CH:24]=[CH:25][C:20]4=[N:19][CH:18]=3)=[O:16])[CH:13]=2)[N:4]=1)(=[O:39])=[O:38]

参加物

5

反応物 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 71280825N-(5-(5-(hydroxymethyl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide

生成物 1

HCID 86677447(3-(3-(Imidazo[1,2-a]pyridine-3-carboxamido)-4-methylphenyl)-1,2,4-oxadiazol-5-yl)methyl methanesulfonate収率 70.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of N-(5-(5-(hydroxymethyl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide (43) (210 mg, 0.6 mmol) and DIEA (0.32 mL, 1.8 mmol) in DCM (5 mL) was added MsCl (138 mg, 1.2 mmol). The mixture was stirred at room temperature for 10 minutes then subjected to standard aqueous work up. The crude product was purified by silica chromatography to yield (3-(3-(imidazo[1,2-a]pyridine-3-carboxamido)-4-methylphenyl)-1,2,4-oxadiazol-5-ylmethyl methanesulfonate (44) (180 mg, 70% yield). MS m/z 428.1 (M+1)+.

後処理

  1. customThe crude product was purified by silica chromatography

出典と根拠

ORDレコード
ord-1409e36b76ed41fc83a5272aa2b662bd
出典データセット
uspto-grants-2015_05
特許番号
US09023839B2

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