Benzylamine → (S)-2-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-N-[1-benzylcarbamoyl-2-(3,4-dichloro-phenyl)-ethyl]-4-chloro-benzamide

HRID 1593885Notes

Reaction equation

[N:1]1[S:5][N:4]=[C:3]2[C:6]([S:10]([NH:13][C:14]3[CH:35]=[C:34]([Cl:36])[CH:33]=[CH:32][C:15]=3[C:16]([NH:18][C@@H:19]([CH2:23][C:24]3[CH:29]=[CH:28][C:27]([Cl:30])=[C:26]([Cl:31])[CH:25]=3)[C:20](O)=[O:21])=[O:17])(=[O:12])=[O:11])=[CH:7][CH:8]=[CH:9][C:2]=12.[CH2:37]([NH2:44])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>>[N:1]1[S:5][N:4]=[C:3]2[C:6]([S:10]([NH:13][C:14]3[CH:35]=[C:34]([Cl:36])[CH:33]=[CH:32][C:15]=3[C:16]([NH:18][C@H:19]([C:20](=[O:21])[NH:44][CH2:37][C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[CH2:23][C:24]3[CH:29]=[CH:28][C:27]([Cl:30])=[C:26]([Cl:31])[CH:25]=3)=[O:17])(=[O:12])=[O:11])=[CH:7][CH:8]=[CH:9][C:2]=12

Participants

Reactant 2

HCID 7504Benzylamine

HCID 45255234(S)-2-[2-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-chloro-benzoylamino]-3-(3,4-dichloro-phenyl)-propionic acid

Product 1

HCID 58999926(S)-2-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-N-[1-benzylcarbamoyl-2-(3,4-dichloro-phenyl)-ethyl]-4-chloro-benzamideYield 33%

Procedure

The title compound (19 mg, 33%) was obtained from (S)-2-[2-(benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-chloro-benzoylamino]-3-(3,4-dichloro-phenyl)-propionic acid and benzyl amine as in Example 1, Part C. HPLC: RT=10.73 min. MS (ESI−): mass calcd. for C29H22Cl3N5O4S2, 675.01; m/z found, 672/674 [M−H]−. 1H NMR (500 MHz, CDCl3): 11.59 (s, 1H), 8.38 (dd, J=7.1, 0.7, 1H), 8.20 (d, J=8.8, 1H), 7.74-7.71 (m, 2H), 7.37-7.25 (m, 5H), 7.13-7.11 (m, 2H), 7.03-6.98 (m, 1H), 6.96-6.87 (m, 2H), 5.79-5.71 (m, 1H), 4.66-4.61 (m, 1H), 4.50-4.45 (m, 1H), 4.33-4.29 (m, 1H), 3.14-3.10 (m, 1H), 3.00-2.96 (m, 1H),

Sources & evidence

ORD record: ord-314dfd6932dd4f5489ff7f4d84fb905e
Source dataset: uspto-grants-2007_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07297816B2

Reaction notes

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