Tetrahydrofuran → N-{2-[5-(Hydroxymethyl)-1,3-thiazol-2-yl]-1-(methoxymethyl)-1H-indol-7-yl}-N-methylthiophene-2-sulfonamide

HRID 1851378ノート

反応式

HRID 1851378 の反応式
[CH3:1][O:2][CH2:3][N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[N:13]([CH3:22])[S:14]([C:17]2[S:18][CH:19]=[CH:20][CH:21]=2)(=[O:16])=[O:15])[CH:6]=[C:5]1[C:23]1[S:24][C:25]([C:28](OCC)=[O:29])=[CH:26][N:27]=1.O1CCCC1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[NH4+]>C(O)C>[OH:29][CH2:28][C:25]1[S:24][C:23]([C:5]2[N:4]([CH2:3][O:2][CH3:1])[C:12]3[C:7]([CH:6]=2)=[CH:8][CH:9]=[CH:10][C:11]=3[N:13]([CH3:22])[S:14]([C:17]2[S:18][CH:19]=[CH:20][CH:21]=2)(=[O:16])=[O:15])=[N:27][CH:26]=1

参加物

6

反応物 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 21226445Aluminium lithium hydrideHCID 57901593Ethyl 2-{1-(methoxymethyl)-7-[methyl(2-thienylsulfonyl)amino]-1H-indol-2-yl}-1,3-thiazole-5-carboxylate

生成物 1

HCID 57901773N-{2-[5-(Hydroxymethyl)-1,3-thiazol-2-yl]-1-(methoxymethyl)-1H-indol-7-yl}-N-methylthiophene-2-sulfonamide収率 100.1%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
0 °C

実験手順

To a mixture of ethyl 2-{1-(methoxymethyl)-7-[methyl(2-thienylsulfonyl)amino]-1H-indol-2-yl}-1,3-thiazole-5-carboxylate (2.13 g) and tetrahydrofuran (30 mL) was added lithium aluminum hydride (0.21 g) at 0° C., and the mixture was stirred at 0° C. for 30 min. To the reaction mixture was added ethanol (5 mL) and then saturated aqueous ammonium chloride solution (4 mL). The resulting inorganic salt was filtered off, and the filtrate was concentrated. The obtained crystals were subjected to silica gel column chromatography and eluted with ethyl acetate to give the title compound (1.95 g, quantitative) as pale-yellow crystals. melting point 156-157° C.

後処理

  1. filtrationThe resulting inorganic salt was filtered off
  2. concentrationthe filtrate was concentrated
  3. washeluted with ethyl acetate

出典と根拠

ORDレコード
ord-56bc1f4c55e34099bedd06d9afc3af86
出典データセット
uspto-grants-2015_02
特許番号
US08957070B2

反応ノート

読み込み中…