2-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-chlorobenzoic acid → HCID 11556194, compound

HRID 2265241Notes

Reaction equation

HRID 2265241 reaction equation
[N:1]1[S:5][N:4]=[C:3]2[C:6]([S:10]([NH:13][C:14]3[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:15]=3[C:16](O)=[O:17])(=[O:12])=[O:11])=[CH:7][CH:8]=[CH:9][C:2]=12.C[O:25][C:26](=[O:39])[C@@H:27]([NH2:38])[C@@H:28]([C:30]1[CH:35]=[CH:34][C:33]([Cl:36])=[C:32]([Cl:37])[CH:31]=1)[CH3:29]>>[N:1]1[S:5][N:4]=[C:3]2[C:6]([S:10]([NH:13][C:14]3[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:15]=3[C:16]([NH:38][C@@H:27]([C@@H:28]([C:30]3[CH:35]=[CH:34][C:33]([Cl:36])=[C:32]([Cl:37])[CH:31]=3)[CH3:29])[C:26]([OH:25])=[O:39])=[O:17])(=[O:12])=[O:11])=[CH:7][CH:8]=[CH:9][C:2]=12

Participants

3

Reactant 2

HCID 160906632-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-chlorobenzoic acidHCID 68769642HCID 68769642, compound

Product 1

HCID 11556194HCID 11556194, compound

Procedure

2-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-chloro-benzoic acid was coupled to (2S,3R)-2-amino-3-(3,4-dichloro-phenyl)-butyric acid methyl ester as in EXAMPLE 1, Part C. The resulting methyl ester was hydrolyzed as in EXAMPLE 2, Part E, to afford the title compound. HPLC: RT=10.22 min. MS (ESI−): mass calcd. for C23H17Cl3N4O5S2, 597.97; m/z found, 597/599 [M−H]−. 1H NMR (500 MHz, CDCl3): 11.26 (s, 1H), 8.36 (d, J=7.0, 1H), 8.21 (d, J=8.8, 1H), 7.73-7.70 (m, 2H), 7.37 (d, J=8.3, 1H), 7.27 (m, 1H), 7.23 (d, J=6.4, 1H), 7.04 (dd, J=8.2, 2.0, 1H), 6.96 (dd, J=8.4, 2.0, 1H), 6.44 (d, J=8.6, 1H), 4.97-4.94 (m, 1H), 3.38-3.36 (m, 1H), 1.46 (d, J=7.2, 3H).

Sources & evidence

ORD record
ord-bc8a71c7fab149e6ad26e2455300df75
Source dataset
uspto-grants-2010_12
Patent number
US07855292B2

Reaction notes

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