2-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-4,5-dichlorobenzoic acid → HCID 58999886, compound

HRID 2265306Notes

Reaction equation

HRID 2265306 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:17])[C@H:6]([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([F:15])=[C:11]([Br:16])[CH:10]=1)[NH2:7])[CH3:3].[N:18]1[S:22][N:21]=[C:20]2[C:23]([S:27]([NH:30][C:31]3[CH:39]=[C:38]([Cl:40])[C:37]([Cl:41])=[CH:36][C:32]=3[C:33](O)=[O:34])(=[O:29])=[O:28])=[CH:24][CH:25]=[CH:26][C:19]=12>>[CH2:2]([O:4][C:5](=[O:17])[C@@H:6]([NH:7][C:33](=[O:34])[C:32]1[CH:36]=[C:37]([Cl:41])[C:38]([Cl:40])=[CH:39][C:31]=1[NH:30][S:27]([C:23]1[C:20]2=[N:21][S:22][N:18]=[C:19]2[CH:26]=[CH:25][CH:24]=1)(=[O:29])=[O:28])[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([F:15])=[C:11]([Br:16])[CH:10]=1)[CH3:3]

Participants

3

Reactant 2

HCID 160907562-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-4,5-dichlorobenzoic acidHCID 68772659HCID 68772659, compound

Product 1

HCID 58999886HCID 58999886, compound

Procedure

The title compound was prepared from 3-bromo-4-fluoro-L-phenylalanine ethyl ester hydrochloride and 2-(benzo[1,2,5]thiadiazole-4-sulfonylamino)-4,5-dichloro-benzoic acid as in Example 1, Part C. HPLC: RT=10.96 min. MS (ESI−): mass calcd. for C22H15Cl3N4O5S2, 676.36; m/z found, 673/675 [M−H]−. 1H NMR (400 MHz, CDCl3): 11.20 (s, 1H), 8.36 (dd, J=7.0, 0.8, 1H), 8.23 (dd, J=8.8, 0.9, 1H), 7.86 (s, 1H), 7.73 (dd, J=8.8, 7.1, 1H), 7.34 (s, 1H), 7.29 (dd, J=6.5, 1.9, 1H), 7.07-6.99 (m, 2H), 6.59 (d, J=7.0, 1H), 4.89 (q, J=5.8, 1H), 4.27 (q, J=7.1, 2H), 3.17 (d, J=5.8, 1H), 1.33 (t, J=7.2, 3H).

Sources & evidence

ORD record
ord-47b5757844164026811d1cc59e467899
Source dataset
uspto-grants-2010_12
Patent number
US07855292B2

Reaction notes

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