Hydrochloric Acid → HCID 57901849, compound

HRID 1851594Notes

Reaction equation

[OH:1][CH2:2][C:3]1[S:4][CH:5]=[CH:6][C:7]=1[S:8]([N:11]([C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:21]=1[N:20](COC)[C:19]([C:25]1[S:26][CH:27]=[CH:28][N:29]=1)=[CH:18]2)[CH3:12])(=[O:10])=[O:9].Br[CH2:31][C:32]([OH:34])=[O:33].[H-].[Na+].Cl>O1CCCC1.O>[CH3:12][N:11]([C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:21]=1[NH:20][C:19]([C:25]1[S:26][CH:27]=[CH:28][N:29]=1)=[CH:18]2)[S:8]([C:7]1[CH:6]=[CH:5][S:4][C:3]=1[CH2:2][O:1][CH2:31][C:32]([OH:34])=[O:33])(=[O:10])=[O:9]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 2-(hydroxymethyl)-N-[1-(methoxymethyl)-2-(1,3-thiazol-2-yl)-1H-indol-7-yl]-N-methylthiophene-3-sulfonamide (480 mg) and bromoacetic acid (178 mg) in tetrahydrofuran (10 mL) was added sodium hydride (60% in oil, 95 mg), and the mixture was stirred at 80° C. for 12 hr. Hydrochloric acid (3 mL) was added to the reaction mixture, and the mixture was stirred at 80° C. for 5 hr. Water was added to the reaction mixture, and the mixture was 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 (ethyl acetate) to give the title compound (98 mg, yield 22%) as pale-yellow crystals. melting point 189° C.

Workup

stirringthe mixture was stirred at 80° C. for 5 hr
extractionthe mixture was extracted with ethyl acetate
washThe ethyl acetate layer was washed with saturated brine
dry with materialdried (MgSO4)
concentrationconcentrated

Sources & evidence

ORD record: ord-342c6a5cdba14cd98a7fd17c52a5681e
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08957070B2

Reaction notes

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