3-oxo-3,4-dihydro-2H-1,4-benzothiazine-6-carboxylic acid → (3S,4R)-1-[2-(7-methoxy-quinoxalin-2-ylsulfanyl)-ethyl]-4-[(3-oxo-3,4-dihydro-2H-benzo[1,4]thiazine-6-carbonyl)-amino]-piperidine-3-carboxylic acid ethyl ester
Reaction equation
[CH2:1]([O:3][C:4]([C@@H:6]1[C@H:11]([NH2:12])[CH2:10][CH2:9][N:8]([CH2:13][CH2:14][S:15][C:16]2[CH:25]=[N:24][C:23]3[C:18](=[CH:19][C:20]([O:26][CH3:27])=[CH:21][CH:22]=3)[N:17]=2)[CH2:7]1)=[O:5])[CH3:2].[O:28]=[C:29]1[NH:34][C:33]2[CH:35]=[C:36]([C:39](O)=[O:40])[CH:37]=[CH:38][C:32]=2[S:31][CH2:30]1>>[CH2:1]([O:3][C:4]([C@@H:6]1[C@H:11]([NH:12][C:39]([C:36]2[CH:37]=[CH:38][C:32]3[S:31][CH2:30][C:29](=[O:28])[NH:34][C:33]=3[CH:35]=2)=[O:40])[CH2:10][CH2:9][N:8]([CH2:13][CH2:14][S:15][C:16]2[CH:25]=[N:24][C:23]3[C:18](=[CH:19][C:20]([O:26][CH3:27])=[CH:21][CH:22]=3)[N:17]=2)[CH2:7]1)=[O:5])[CH3:2]Participants
3
Reactant 2
Product 1
Procedure
The title compound is prepared as an orange semisolid (280 mg, 87% yield) following Scheme 3 and in analogy to Example 35 using (3S,4R)-4-amino-1-[2-(7-methoxy-quinoxalin-2-ylsulfanyl)-ethyl]-piperidine-3-carboxylic acid ethyl ester (216 mg, 0.50 mmol, 1.0 eq) and 3-oxo-3,4-dihydro-2H-benzo[1,4]thiazine-6-carboxylic acid (113 mg, 0.50 mmol, 1.0 eq) as starting material.
Sources & evidence
- ORD record
- ord-353cd347d6314bfb8669e04fc39d40de
- Source dataset
- uspto-grants-2015_01
- Patent number
- US08927542B2
Reaction notes
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