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

HRID 1851378Notes

Reaction equation

[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

Participants

Conditions

Temperature: 0 °C

Procedure

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.

Workup

filtrationThe resulting inorganic salt was filtered off
concentrationthe filtrate was concentrated
washeluted with ethyl acetate

Sources & evidence

ORD record: ord-56bc1f4c55e34099bedd06d9afc3af86
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08957070B2

Reaction notes

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