Hydrochloric Acid → Ethyl N-[2-(1,3-thiazol-2-yl)-1H-indol-7-yl]-N-(2-thienylsulfonyl)aminoacetate

HRID 1851519Notes

Reaction equation

COC[N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[N:13]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[S:14]([C:17]2[S:18][CH:19]=[CH:20][CH:21]=2)(=[O:16])=[O:15])[CH:6]=[C:5]1[C:28]1[S:29][CH:30]=[CH:31][N:32]=1.Cl.C(=O)(O)[O-].[Na+]>C(O)C>[S:29]1[CH:30]=[CH:31][N:32]=[C:28]1[C:5]1[NH:4][C:12]2[C:7]([CH:6]=1)=[CH:8][CH:9]=[CH:10][C:11]=2[N:13]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[S:14]([C:17]1[S:18][CH:19]=[CH:20][CH:21]=1)(=[O:15])=[O:16]

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of ethyl N-[1-(methoxymethyl)-2-(1,3-thiazol-2-yl)-1H-indol-7-yl]-N-(2-thienylsulfonyl)aminoacetate (0.31 g), concentrated hydrochloric acid (0.5 mL) and ethanol (6 mL) was stirred at 70° C. for 6 hr. The reaction mixture was neutralized with aqueous sodium bicarbonate, and extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The obtained residue was subjected to silica gel column chromatography and the title compound (0.17 g, yield 60%) was obtained as colorless crystals from a fraction eluted with ethyl acetate-hexane (1:1, volume ratio). The crystals were recrystallized from ethyl acetate-hexane. melting point 135-137° C.

Workup

extractionextracted with ethyl acetate
washThe ethyl acetate layer was washed with saturated brine
dry with materialdried (MgSO4)
concentrationconcentrated

Sources & evidence

ORD record: ord-795d7f2694644068a2e7533fdb463874
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08957070B2

Reaction notes

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