Hydrochloric Acid → HCID 59135865, compound

HRID 1960508Notes

Reaction equation

C([O:3][C:4](=[O:31])[CH2:5][CH:6]1[S:10][C:9]([C:11]2[NH:12][C:13]3[C:18]([CH:19]=2)=[CH:17][CH:16]=[CH:15][C:14]=3[N:20]([CH3:30])[S:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=2)(=[O:23])=[O:22])=[N:8][CH2:7]1)C.[OH-].[K+].Cl>O1CCCC1.CO.O.C(OCC)(=O)C>[CH3:30][N:20]([S:21]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=1)(=[O:23])=[O:22])[C:14]1[CH:15]=[CH:16][CH:17]=[C:18]2[C:13]=1[NH:12][C:11]([C:9]1[S:10][CH:6]([CH2:5][C:4]([OH:31])=[O:3])[CH2:7][N:8]=1)=[CH:19]2

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of ethyl(2-{7-[methyl(pyridin-2-ylsulfonyl)amino]-1H-indol-2-yl}-4,5-dihydro-1,3-thiazol-5-yl)acetate (470 mg) in tetrahydrofuran (6 ml) and methanol (6 mL) was added a solution of potassium hydroxide (85% purity, 170 mg) in water (2.5 mL), and the mixture was stirred at 0° C. for 1 hr, and then at room temperature for 3 hr. The reaction mixture was diluted with ethyl acetate, and neutralized with 1M hydrochloric acid. The ethyl acetate layer was washed with saturated brine, dried (MgSO4), and concentrated. The residue was recrystallized from a mixed solvent of ethyl acetate-hexane to give the title compound (400 mg, yield 91%) as white crystals. MS:431(MH+). melting point 231-233° C.

Workup

waitat room temperature for 3 hr
washThe ethyl acetate layer was washed with saturated brine
dry with materialdried (MgSO4)
concentrationconcentrated
customThe residue was recrystallized from a mixed solvent of ethyl acetate-hexane

Sources & evidence

ORD record: ord-891c9eaae5a4410d85242943e8e17994
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08410087B2

Reaction notes

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