2,1,3-Benzothiadiazole, 4-chlorosulfonyl- → 2-[2-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-4,5-dichloro-benzoylamino]-3-phenyl-propionic acid
Reaction equation
C[O:2][C:3](=[O:24])[CH:4]([NH:12][C:13](=[O:23])[C:14]1[CH:19]=[C:18]([Cl:20])[C:17]([Cl:21])=[CH:16][C:15]=1[NH2:22])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[N:25]1[S:29][N:28]=[C:27]2[C:30]([S:34](Cl)(=[O:36])=[O:35])=[CH:31][CH:32]=[CH:33][C:26]=12>>[N:25]1[S:29][N:28]=[C:27]2[C:30]([S:34]([NH:22][C:15]3[CH:16]=[C:17]([Cl:21])[C:18]([Cl:20])=[CH:19][C:14]=3[C:13]([NH:12][CH:4]([CH2:5][C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:3]([OH:2])=[O:24])=[O:23])(=[O:35])=[O:36])=[CH:31][CH:32]=[CH:33][C:26]=12Participants
3
Procedure
This compound was prepared from 2-(2-amino-4,5-dichloro-benzoylamino)-3-phenyl-propionic acid methyl ester and benzo[1,2,5]thiadiazole-4-sulfonyl chloride as in EXAMPLE 2, Parts D and E. HPLC: RT=10.10 min. MS (ESI−): mass calcd. for C22H16Cl2N4O5S2, 551.4; m/z found, 550 [M−H]−. 1H NMR (400 MHz, CDCl3): 11.11 (s, 1H), 8.33 (dd, J=7.1, 0.9, 1H), 8.20 (dd, J=8.8, 0.8, 1H), 7.83 (s, 1H), 7.70 (dd, J=8.8, 7.1, 1H), 7.28 (m, 3H), 7.20 (s, 1H), 7.13 (dd, J=7.4, 1.7, 2H), 6.42 (d, J=7.5, 1H), 5.00 (dd, J=13.3, 6.0, 1H), 3.32 (dd, J=14.1, 5.7, 1H), 3.23 (dd, J=14.1, 6.1, 1H).
Sources & evidence
- ORD record
- ord-8876ee0e6be040f59b819ad493ed81e9
- Source dataset
- uspto-grants-2010_12
- Patent number
- US07855292B2
Reaction notes
Loading…