Acetic Acid → HCID 66818109, compound

HRID 1755022Notes

Reaction equation

CS[C:3]1[S:4][CH2:5][CH2:6][N:7]=1.C(O)(=O)C.[NH2:12][C:13]1[CH:18]=[C:17]([CH3:19])[C:16](/[CH:20]=[CH:21]/[S:22]([N:25]2[CH2:41][CH2:40][C:28]3([C:32](=[O:33])[NH:31][C:30]([CH:34]4[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]4)=[N:29]3)[CH2:27][CH2:26]2)(=[O:24])=[O:23])=[C:15]([CH3:42])[CH:14]=1>CCO.C(OCC)(=O)C>[CH:34]1([C:30]2[NH:31][C:32](=[O:33])[C:28]3([CH2:27][CH2:26][N:25]([S:22](/[CH:21]=[CH:20]/[C:16]4[C:17]([CH3:19])=[CH:18][C:13]([NH:12][C:3]5[S:4][CH2:5][CH2:6][N:7]=5)=[CH:14][C:15]=4[CH3:42])(=[O:23])=[O:24])[CH2:41][CH2:40]3)[N:29]=2)[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1

Participants

Conditions

Temperature: 80 °C

Procedure

2-(Methylthio)-2-thiazoline (19 μL, 0.17 mmol) and acetic acid (1.2 ml) were added to a solution of 8-[(E)-2-(4-amino-2,6-dimethyl-phenyl)vinyl]sulfonyl-3-cyclohexyl-2,4,8-triazaspiro[4.5]dec-3-en-1-one (74 mg, 0.16 mmol) in EtOH (2.5 ml) at room temperature, and the mixture was heated with stirring at 80° C. for 16 hours. The reaction solution was diluted with ethyl acetate, and the organic layer was then sequentially washed with water and saturated brine and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate) to give 2-cyclohexyl-8-{(E)-2-[4-(4,5-dihydro-thiazol-2-ylamino)-2,6-dimethyl-phenyl]-ethenesulfonyl}-1,3,8-triaza-spiro[4.5]dec-1-en-4-one (46.1 mg, 52%).

Workup

temperaturethe mixture was heated
washthe organic layer was then sequentially washed with water and saturated brine
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record: ord-31de87b6f0b5467c8bf6406e1ea5fbef
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09169254B2

Reaction notes

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