Ethyl 2-amino-4,5,6,7-tetrahydro-1,3-benzothiazole-4-carboxylate → 2-{[1-(2-Methoxy-5-methyl-benzenesulfonyl)-1,2,3,4-tetrahydro-quinoline-7-carbonyl]-amino}-4,5,6,7-tetrahydro-benzothiazole-4-carboxylic acid ethyl ester
Reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[C:11]2[N:12]=[C:13]([NH2:15])[S:14][C:10]=2[CH2:9][CH2:8][CH2:7]1)=[O:5])[CH3:2].[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][C:19]=1[S:25]([N:28]1[C:37]2[C:32](=[CH:33][CH:34]=[C:35]([C:38](O)=[O:39])[CH:36]=2)[CH2:31][CH2:30][CH2:29]1)(=[O:27])=[O:26]>>[CH2:1]([O:3][C:4]([CH:6]1[C:11]2[N:12]=[C:13]([NH:15][C:38]([C:35]3[CH:36]=[C:37]4[C:32]([CH2:31][CH2:30][CH2:29][N:28]4[S:25]([C:19]4[CH:20]=[C:21]([CH3:24])[CH:22]=[CH:23][C:18]=4[O:17][CH3:16])(=[O:27])=[O:26])=[CH:33][CH:34]=3)=[O:39])[S:14][C:10]=2[CH2:9][CH2:8][CH2:7]1)=[O:5])[CH3:2]Participants
3
Reactant 2
Product 1
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 2-amino-4,5,6,7-tetrahydro-benzothiazole-4-carboxylic acid ethyl ester and 1-(2-methoxy-5-methyl-benzenesulfonyl)-1,2,3,4-tetrahydro-quinoline-7-carboxylic acid and yielded 2-{[1-(2-methoxy-5-methyl-benzenesulfonyl)-1,2,3,4-tetrahydro-quinoline-7-carbonyl]-amino}-4,5,6,7-tetrahydro-benzothiazole-4-carboxylic acid ethyl ester, which was hydrolyzed to 2-{[1-(2-methoxy-5-methyl-benzenesulfonyl)-1,2,3,4-tetrahydro-quinoline-7-carbonyl]-amino}-4,5,6,7-tetrahydro-benzothiazole-4-carboxylic acid in step 4, MS (ISP): m/e=540.3 (M−H).
Sources & evidence
- ORD record
- ord-a6782c1f9afb43f2b57c615066df6594
- Source dataset
- uspto-grants-2010_09
- Patent number
- US07799933B2
Reaction notes
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