P-Anisidine → HCID 53345317, compound

HRID 1464992Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:20])[NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=2)=[CH:4][C:3]=1[NH:21][C:22]([C:24]1[C:28]2[N:29]=[CH:30][N:31]=[C:32](S(C)=O)[C:27]=2[S:26][CH:25]=1)=[O:23].CCN(C(C)C)C(C)C.[CH3:45][O:46][C:47]1[CH:52]=[CH:51][C:50]([NH2:53])=[CH:49][CH:48]=1>O1CCOCC1.C(OCC)(=O)C>[CH3:45][O:46][C:47]1[CH:52]=[CH:51][C:50]([NH:53][C:32]2[C:27]3[S:26][CH:25]=[C:24]([C:22]([NH:21][C:3]4[CH:4]=[C:5]([C:8](=[O:20])[NH:9][C:10]5[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:18])([F:19])[F:17])[CH:11]=5)[CH:6]=[CH:7][C:2]=4[CH3:1])=[O:23])[C:28]=3[N:29]=[CH:30][N:31]=2)=[CH:49][CH:48]=1

Participants

Conditions

Temperature: 120 °C

Procedure

N-(2-methyl-5-(3-(trifluoromethyl)phenylcarbamoyl)phenyl)-4-(methylsulfinyl)thieno[3,2-d]pyrimidine-7-carboxamide (30 mg, 0.060 mmol) was dissolved in dioxane (1 mL) and DIPEA (20 μL, 0.119 mmol) and 4-methoxybenzeneamine (37 mg, 0.298 mmol) were added thereto. The reaction mixture was stirred at 120° C. for 18 hours, cooled to room temperature, diluted with ethyl acetate and washed with a brine. The organic layer was dried with MgSO4, filtered and concentrated under reduced pressure. The resulting mixture was purified by silica gel chromatography to obtain the title compound (28 mg, 81% yield).

Workup

temperaturecooled to room temperature
washwashed with a brine
dry with materialThe organic layer was dried with MgSO4
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe resulting mixture was purified by silica gel chromatography

Sources & evidence

ORD record: ord-6143811d065547b2996062ae851c79dc
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08999973B2

Reaction notes

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