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

HRID 2265278Notes

Reaction equation

HRID 2265278 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]([OH:22])=O)=[O:17])(=[O:12])=[O:11])=[CH:7][CH:8]=[CH:9][C:2]=12.[Cl:37][C:38]1[CH:39]=[C:40]([CH:43]=[CH:44][CH:45]=1)[CH2:41][NH2:42]>>[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:22])[NH:42][CH2:41][C:40]3[CH:43]=[CH:44][CH:45]=[C:38]([Cl:37])[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:11])=[O:12])=[CH:7][CH:8]=[CH:9][C:2]=12

Participants

3

Reactant 2

HCID 77802Benzenemethanamine, 3-chloro-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 58999871(S)-2-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-chloro-N-[1-(3-chloro-benzylcarbamoyl)-2-(3,4-dichloro-phenyl)-ethyl]-benzamideYield 48%

Procedure

The title compound (29 mg, 48%) was obtained from (S)-2-[2-(benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-chloro-benzoylamino]-3-(3,4-dichloro-phenyl)-propionic acid and 3-chlorobenzylamine as in Example 1, Part C. HPLC: RT=10.95 min. MS (ESI−): mass calcd. for C29H21Cl4N5O4S2, 709.45; m/z found, 706/708 [M−H]−. 1H NMR (500 MHz, CDCl3): 11.55 (s, 1H), 8.39 (dd, J=7.0, 0.9, 1H), 8.22 (dd, J=8.8, 0.8, 1H), 7.73 (dd, J=8.8, 7.1, 1H), 7.70 (d, J=2.0, 1H), 7.38-7.30 (m, 3H), 7.16 (d, J=0.5, 1H), 7.05-6.99 (m, 2H), 6.96 (dd, J=8.5, 2.0, 1H), 6.88-6.81 (m, 1H), 5.87-5.80 (m, 1H), 4.70-4.61 (m, 1H), 4.49-4.41 (m, 1H), 4.34-4.26 (m, 1H), 3.17-3.09 (m, 1H), 3.06-2.96 (m, 1H).

Sources & evidence

ORD record
ord-4a9db178e8d14d99881e527e11ebc422
Source dataset
uspto-grants-2010_12
Patent number
US07855292B2

Reaction notes

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