3-Fluorobenzenesulfonyl Chloride → HCID 68697776, compound

HRID 2235147Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:25])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]([C:14]2[CH:23]=[C:22]3[C:17]([CH2:18][CH2:19][CH2:20][NH:21]3)=[CH:16][CH:15]=2)=[O:13])=[CH:7][C:6]=1[F:24])[CH3:2].[F:26][C:27]1[CH:28]=[C:29]([S:33](Cl)(=[O:35])=[O:34])[CH:30]=[CH:31][CH:32]=1>>[CH2:1]([O:3][C:4](=[O:25])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]([C:14]2[CH:23]=[C:22]3[C:17]([CH2:18][CH2:19][CH2:20][N:21]3[S:33]([C:29]3[CH:30]=[CH:31][CH:32]=[C:27]([F:26])[CH:28]=3)(=[O:35])=[O:34])=[CH:16][CH:15]=2)=[O:13])=[CH:7][C:6]=1[F:24])[CH3:2]

Participants

Reactant 2

HCID 27342583-Fluorobenzenesulfonyl Chloride

HCID 68699370HCID 68699370, compound

Product 1

HCID 68697776HCID 68697776, compound

Procedure

2-Fluoro-4-{[1-(3-fluoro-benzenesulfonyl)-1,2,3,4-tetrahydro-quinoline-7-carbonyl]-amino}-benzoic acid, m/z (ES+): 473.24 (M+H+.), was prepared in analogy to example 40, steps 1 to 5. Step 2 was performed using 4-amino-2-fluorobenzoic acid ethyl ester and yielded 2-fluoro-4-[(quinoline-7-carbonyl)-amino]-benzoic acid ethyl ester, which was reduced to 2-fluoro-4-[(1,2,3,4-tetrahydro-quinoline-7-carbonyl)-amino]-benzoic acid ethyl ester in step 3. Step 4 was performed using 3-fluoro-benzenesulfonyl chloride, yielding 2-fluoro-4-{[1-(3-fluoro-benzenesulfonyl)-1,2,3,4-tetrahydro-quinoline-7-carbonyl]-amino}-benzoic acid ethyl ester, which was hydrolyzed in step 5.

Sources & evidence

ORD record: ord-db8f0c5c6739477d9389dc3554864770
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07713996B2

Reaction notes

Loading…