Water → HCID 131729761, compound

HRID 217290Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[SH:9].C(=O)([O-])[O-].[K+].[K+].[Cl:16][CH:17]1[CH:29]=[C:21]2[CH2:22][O:23][CH2:24][C:25]3[CH:26]=[CH:27][CH:28]=[C:19]([C:20]=32)[C:18]1([C:32]1[N:37]=[C:36](S(C)=O)[N:35]=[C:34]([NH2:41])[N:33]=1)[C:30]#[N:31].O>CN(C)C=O.C(OCC)(=O)C>[Cl:16][CH:17]1[CH:29]=[C:21]2[CH2:22][O:23][CH2:24][C:25]3[CH:26]=[CH:27][CH:28]=[C:19]([C:20]=32)[C:18]1([C:32]1[N:37]=[C:36]([S:9][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[O:2][CH3:1])[N:35]=[C:34]([NH2:41])[N:33]=1)[C:30]#[N:31]

Participants

Conditions

Temperature: 85 °C

Procedure

2-Methoxythiophenol (39 mg, 0.278 mmol) was added to a suspension of potassium carbonate (95.7 mg, 0.692 mmol) and 4-(5-chloro-6-cyano-1H,3H benzo[de]isochromen-6-yl)-6-methylsulfinyl-[1,3,5]triazin-2-ylamine (50 mg, 0.139 mmol) in N,N-dimethylformamide (2.5 mL) at room temperature under argon atmosphere. The reaction solution was stirred at 85° C. for 12 hours, and then allowed to return to room temperature. The reaction solution was diluted with ethyl acetate, and then water was added. The organic layer was separated, washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting crude product was purified by silica gel column chromatography using methylene chloride-ethyl acetate (mixing ratio=7:1 to 4:1) and dried under reduced pressure to give the title compound (34 mg, 56%).

Workup

customto return to room temperature
customThe organic layer was separated
washwashed with brine
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe resulting crude product was purified by silica gel column chromatography
customdried under reduced pressure

Sources & evidence

ORD record: ord-388038f62ce74b6c9e988ca5e7e201ae
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08193351B2

Reaction notes

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