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

HRID 1851378노트

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HRID 1851378 반응식
[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

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
0 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-56bc1f4c55e34099bedd06d9afc3af86
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08957070B2

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