p-Toluenesulfonic acid monohydrate → HCID 178463975, compound

HRID 1620576Notes

Reaction equation

[F:1][C:2]([F:38])([F:37])[C:3]1[CH:32]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:30]=[CH:29][C:4]=1[CH2:5][N:6]1[CH2:11][CH2:10][CH:9](/[CH:12]=[C:13]2/[C:14]([NH:19][CH2:20]/[CH:21]=[CH:22]\[CH2:23][N:24]([CH2:27][CH3:28])[CH2:25][CH3:26])=[N:15][C:16](=[O:18])[S:17]/2)[CH2:8][CH2:7]1.O.[S:40]([C:44]1[CH:50]=[CH:49][C:47]([CH3:48])=[CH:46][CH:45]=1)([OH:43])(=[O:42])=[O:41]>C(OCC)(=O)C>[S:40]([C:44]1[CH:50]=[CH:49][C:47]([CH3:48])=[CH:46][CH:45]=1)([OH:43])(=[O:42])=[O:41].[F:38][C:2]([F:1])([F:37])[C:3]1[CH:32]=[C:31]([C:33]([F:35])([F:36])[F:34])[CH:30]=[CH:29][C:4]=1[CH2:5][N:6]1[CH2:11][CH2:10][CH:9](/[CH:12]=[C:13]2/[C:14]([NH:19][CH2:20]/[CH:21]=[CH:22]\[CH2:23][N:24]([CH2:27][CH3:28])[CH2:25][CH3:26])=[N:15][C:16](=[O:18])[S:17]/2)[CH2:8][CH2:7]1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of (5Z)-5-({1-[2,4-bis(trifluoromethyl)benzyl]piperidin-4-yl}methylidene)-4-{[(2Z)-4-(diethylamino)but-2-en-1-yl]amino}-1,3-thiazol-2(5H)-one (162 mg) in ethyl acetate (3 mL) was added tosylic acid monohydrate (55 mg) at room temperature. The reaction mixture was stirred at 60° C. for 5 min. The solvent was evaporated under reduced pressure, and the residue was recrystallized from ethyl acetate/heptane to give the title compound (179 mg).

Workup

customThe solvent was evaporated under reduced pressure
customthe residue was recrystallized from ethyl acetate/heptane

Sources & evidence

ORD record: ord-dde05d90412d40b0988e76eb3ce3aed7
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772277B2

Reaction notes

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