Ethyl 4-Amino-2-fluorobenzoate → HCID 68694892, compound

HRID 2235146Notes

Reaction equation

HRID 2235146 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([NH:11][C:12]([C:14]2[CH:23]=[C:22]3[C:17]([CH2:18][CH2:19][CH2:20][N:21]3S(C3C=CC=C(F)C=3)(=O)=O)=[CH:16][CH:15]=2)=[O:13])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH2:34](OC(=O)C1C=CC(N)=CC=1F)[CH3:35]>>[CH2:34]([O:6][C:4](=[O:5])[C:3]1[CH:7]=[CH:8][C:9]([NH:11][C:12]([C:14]2[CH:23]=[C:22]3[C:17]([CH:18]=[CH:19][CH:20]=[N:21]3)=[CH:16][CH:15]=2)=[O:13])=[CH:10][C:2]=1[F:1])[CH3:35]

Participants

3

Reactant 2

HCID 10797532Ethyl 4-Amino-2-fluorobenzoateHCID 16050617HCID 16050617, compound

Product 1

HCID 68694892HCID 68694892, 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-7d92e025f04d4cd4b97cf3272aa503ec
Source dataset
uspto-grants-2010_05
Patent number
US07713996B2

Reaction notes

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