(5-Amino-[1,2,4]thiadiazol-3-yl)-acetic acid allyl ester → (5-{[1-(2-Methoxy-5-methyl-benzenesulfonyl)-1,2,3,4-tetrahydro-quinoline-7-carbonyl]-amino}-[1,2,4]thiadiazol-3-yl)-acetic acid allyl ester

HRID 1715847Notes

Reaction equation

HRID 1715847 reaction equation
[CH2:1]([O:4][C:5](=[O:13])[CH2:6][C:7]1[N:11]=[C:10]([NH2:12])[S:9][N:8]=1)[CH:2]=[CH2:3].[CH3:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][C:17]=1[S:23]([N:26]1[C:35]2[C:30](=[CH:31][CH:32]=[C:33]([C:36](O)=[O:37])[CH:34]=2)[CH2:29][CH2:28][CH2:27]1)(=[O:25])=[O:24]>>[CH2:1]([O:4][C:5](=[O:13])[CH2:6][C:7]1[N:11]=[C:10]([NH:12][C:36]([C:33]2[CH:34]=[C:35]3[C:30]([CH2:29][CH2:28][CH2:27][N:26]3[S:23]([C:17]3[CH:18]=[C:19]([CH3:22])[CH:20]=[CH:21][C:16]=3[O:15][CH3:14])(=[O:25])=[O:24])=[CH:31][CH:32]=2)=[O:37])[S:9][N:8]=1)[CH:2]=[CH2:3]

Participants

3

Reactant 2

HCID 68433648(5-Amino-[1,2,4]thiadiazol-3-yl)-acetic acid allyl esterHCID 684338071-(2-Methoxy-5-methyl-benzenesulfonyl)-1,2,3,4-tetrahydro-quinoline-7-carboxylic acid

Product 1

HCID 68434617(5-{[1-(2-Methoxy-5-methyl-benzenesulfonyl)-1,2,3,4-tetrahydro-quinoline-7-carbonyl]-amino}-[1,2,4]thiadiazol-3-yl)-acetic acid allyl ester

Procedure

1-(2-Methoxy-5-methyl-benzenesulfonyl)-1,2,3,4-tetrahydro-quinoline-7-carboxylic acid was converted to the title compound in analogy to example 8, steps 3 and 4. Step 3 was performed using (5-amino-[1,2,4]thiadiazol-3-yl)-acetic acid allyl ester and 1-(2-methoxy-5-methyl-benzenesulfonyl)-1,2,3,4-tetrahydro-quinoline-7-carboxylic acid and yielded (5-{[1-(2-methoxy-5-methyl-benzenesulfonyl)-1,2,3,4-tetrahydro-quinoline-7-carbonyl]-amino}-[1,2,4]thiadiazol-3-yl)-acetic acid allyl ester, which was hydrolyzed to (5-{[1-(2-methoxy-5-methyl-benzenesulfonyl)-1,2,3,4-tetrahydro-quinoline-7-carbonyl]-amino}-[1,2,4]thiadiazol-3-yl)-acetic acid in step 4, MS (ISP): m/e=501.1 (M−H).

Sources & evidence

ORD record
ord-b3c5c72f9dc54db9867aaf88901b599c
Source dataset
uspto-grants-2010_09
Patent number
US07799933B2

Reaction notes

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