Quinoline → N-{2-Amino-6-methyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridin-4-yl}-3-chlorobenzenesulfonamide

HRID 573604Notes

Reaction equation

[NH2:1][C:2]1[S:25][C:5]2=[N:6][C:7]([CH3:24])=[C:8](C(O)=O)[C:9]([NH:10][S:11]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=3)(=[O:13])=[O:12])=[C:4]2[C:3]=1[C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([O:32][CH3:33])[CH:27]=1.N1C2C(=CC=CC=2)C=CC=1>[Cu]>[NH2:1][C:2]1[S:25][C:5]2=[N:6][C:7]([CH3:24])=[CH:8][C:9]([NH:10][S:11]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=3)(=[O:12])=[O:13])=[C:4]2[C:3]=1[C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([O:32][CH3:33])[CH:27]=1

Participants

Conditions

Temperature: 200 °C

Procedure

A mixture of 2-amino-4-{[(3-chlorophenyl)sulfonyl]amino}-6-methyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridine-5-carboxylic acid (Description 84) (388 mg, 0.770 mmol), copper (245 mg, 3.85 mmol) and quinoline (3 mL, 25.3 mmol) was heated at 200° C. for ca. 1 h. After cooling to RT, the mixture was purified by normal phase chromatography, eluting with a gradient of 50-70% ethyl acetate in cyclohexane followed by 10% MeOH in DCM, to give the title compound (127 mg). LCMS (A) m/z: 460 [M+1]+, Rt 1.10 min (acidic).

Workup

temperatureAfter cooling to RT
customthe mixture was purified by normal phase chromatography
washeluting with a gradient of 50-70% ethyl acetate in cyclohexane

Sources & evidence

ORD record: ord-5106b5e995d14601a9104709166f2fc2
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09029545B2

Reaction notes

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