Ammonia → HCID 11635635, compound

HRID 2265188Notes

Reaction equation

[N:1]1[S:5][N:4]=[C:3]2[C:6]([S:10]([NH:13][C:14]3[CH:34]=[C:33]([Cl:35])[C:32]([Cl:36])=[CH:31][C:15]=3[C:16]([NH:18][C@@H:19]([CH2:23][C:24]3[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=3)[C:20](O)=[O:21])=[O:17])(=[O:12])=[O:11])=[CH:7][CH:8]=[CH:9][C:2]=12.[NH3:37]>>[N:1]1[S:5][N:4]=[C:3]2[C:6]([S:10]([NH:13][C:14]3[CH:34]=[C:33]([Cl:35])[C:32]([Cl:36])=[CH:31][C:15]=3[C:16]([NH:18][C@H:19]([C:20](=[O:21])[NH2:37])[CH2:23][C:24]3[CH:25]=[CH:26][C:27]([Cl:30])=[CH:28][CH:29]=3)=[O:17])(=[O:12])=[O:11])=[CH:7][CH:8]=[CH:9][C:2]=12

Participants

Reactant 2

HCID 222Ammonia

HCID 11650018HCID 11650018, compound

Product 1

HCID 11635635HCID 11635635, compoundYield 20%

Procedure

The title compound (3 mg, 20%) was prepared from (S)-2-[2-(benzo[1,2,5]thiadiazole-4-sulfonylamino)-4,5-dichloro-benzoylamino]-3-(4-chloro-phenyl)-propionic acid and NH3 (0.5 M in dioxane) as in Example 1, Part C. HPLC: RT=10.08 min. MS (ESI−): mass calcd. for C22H16Cl3N5O4S2, 582.97; m/z found, 582/584 [M−H]−. 1H NMR (400 MHz, CDCl3): 11.34 (s, 1H), 8.37 (dd, J=7.1, 1.0, 1H), 8.24 (dd, J=8.8, 1.0, 1H), 7.84 (s, 1H), 7.73 (dd, J=8.8, 7.1, 1H), 7.36 (s, 1H), 7.36-7.32 (m, 2H), 7.24-7.20 (m, 2H), 6.84 (br d, J=6.9, 1H), 5.47 (br s, 1H), 5.41 (br s, 1H), 4.68 (ddd, J=8.6, 7.0, 5.0, 1H), 3.18 (dd, J=13.7, 4.9, 1H), 3.01 (dd, J=13.6, 8.6, 1H).

Sources & evidence

ORD record: ord-30f9d54e207e4bcab3b5027759d006f6
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07855292B2

Reaction notes

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