4-Bromo-2-fluoroaniline → Jtp-70902

HRID 75634Notes

Reaction equation

[CH:1]1([N:4]2[C:9](=[O:10])[C:8]3[C:11](OS(C4C=CC(C)=CC=4)(=O)=O)=[CH:12][C:13](=[O:16])[N:14]([CH3:15])[C:7]=3[N:6]([C:28]3[CH:33]=[CH:32][CH:31]=[C:30]([NH:34][S:35]([CH3:38])(=[O:37])=[O:36])[CH:29]=3)[C:5]2=[O:39])[CH2:3][CH2:2]1.[F:40][C:41]1[CH:47]=[C:46]([Br:48])[CH:45]=[CH:44][C:42]=1[NH2:43]>>[Br:48][C:46]1[CH:45]=[CH:44][C:42]([NH:43][C:11]2[C:8]3[C:9](=[O:10])[N:4]([CH:1]4[CH2:3][CH2:2]4)[C:5](=[O:39])[N:6]([C:28]4[CH:29]=[C:30]([NH:34][S:35]([CH3:38])(=[O:37])=[O:36])[CH:31]=[CH:32][CH:33]=4)[C:7]=3[N:14]([CH3:15])[C:13](=[O:16])[CH:12]=2)=[C:41]([F:40])[CH:47]=1

Participants

Reactant 2

HCID 1230504-Bromo-2-fluoroaniline

HCID 59717043HCID 59717043, compound

Product 1

HCID 11527186Jtp-70902Yield 83.1%

Conditions

Temperature: 135 °C

Procedure

To toluene-4-sulfonic acid 3-cyclopropyl-1-(3-methanesulfonylaminophenyl)-8-methyl-2,4,7-trioxo-1,2,3,4,7,8-hexahydropyrido[2,3-d]pyrimidin-5-yl ester 15 (3.5 g) obtained in Step 8 was added 2-fluoro-4-bromoaniline 16 (23 g), and the mixture was stirred under heating at 135° C. for 3 hrs. The reaction mixture was purified by column chromatography (chloroform:acetone=9:1) to give N-{3-[5-(4-bromo-2-fluoro-phenylamino)-3-cyclopropyl-8-methyl-2,4,7-trioxo-3,4,7,8-tetrahydro-2H-pyrido[2,3-d]pyrimidin-1-yl]phenyl}-methanesulfonamide 17 (3.0 g, 83%) as a white solid.

Workup

customThe reaction mixture was purified by column chromatography (chloroform:acetone=9:1)

Sources & evidence

ORD record: ord-d089eb3956a045a49cd665aacd4332ed
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08835443B2

Reaction notes

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