2-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-iodo-benzoic acid → HCID 58999882, compound

HRID 2265282Notes

Reaction equation

HRID 2265282 reaction equation
Cl.C[O:3][C:4](=[O:16])[C@@H:5]([NH2:15])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][C:8]=1[Cl:14].[N:17]1[S:21][N:20]=[C:19]2[C:22]([S:26]([NH:29][C:30]3[CH:38]=[C:37]([I:39])[CH:36]=[CH:35][C:31]=3[C:32](O)=[O:33])(=[O:28])=[O:27])=[CH:23][CH:24]=[CH:25][C:18]=12>>[N:17]1[S:21][N:20]=[C:19]2[C:22]([S:26]([NH:29][C:30]3[CH:38]=[C:37]([I:39])[CH:36]=[CH:35][C:31]=3[C:32]([NH:15][C@@H:5]([CH2:6][C:7]3[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][C:8]=3[Cl:14])[C:4]([OH:3])=[O:16])=[O:33])(=[O:28])=[O:27])=[CH:23][CH:24]=[CH:25][C:18]=12

Participants

3

Reactant 2

HCID 160906642-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-iodo-benzoic acidHCID 68768460HCID 68768460, compound

Product 1

HCID 58999882HCID 58999882, compound

Procedure

(S)-2-tert-Butoxycarbonylamino-3-(2,4-dichloro-phenyl)-propionic acid was treated as in EXAMPLE 2, Part A, to produce (S)-2-amino-3-(2,4-dichloro-phenyl)-propionic acid methyl ester hydrochloride as a white solid. This ester was coupled to 2-(benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-iodo-benzoic acid 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=10.19 min. MS (ESI−): mass calcd. for C22H15Cl2IN4O5S2, 677.32; m/z found, 675/677 [M−H]−. 1H NMR (500 MHz, CDCl3): 11.16 (s, 1H), 8.34 (d, J=7.1, 1H), 8.21 (d, J=8.8, 1H), 8.07-8.05 (m, 1H), 7.71 (dd, J=8.8, 7.1, 1H), 7.40-7.39 (m, 1H), 7.32-7.26 (m, 1H), 7.24-7.22 (m, 2H), 6.94 (d, J=8.3, 1H), 6.53 (d, J=7.5, 1H), 5.02-4.95 (m, 1H), 3.53-3.44 (m, 1H), 3.34-3.24 (m, 1H).

Sources & evidence

ORD record
ord-d60b817b82364f759606cf1e426d36b0
Source dataset
uspto-grants-2010_12
Patent number
US07855292B2

Reaction notes

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