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

HRID 1593886Notes

Reaction equation

HRID 1593886 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.[F:37][C:38]1[CH:45]=[CH:44][C:41]([CH2:42][NH2:43])=[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:43][CH2:42][C:41]3[CH:44]=[CH:45][C:38]([F:37])=[CH:39][CH:40]=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

3

Reactant 2

HCID 673264-FluorobenzylamineHCID 45255234(S)-2-[2-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-chloro-benzoylamino]-3-(3,4-dichloro-phenyl)-propionic acid

Product 1

HCID 58999891(S)-2-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-chloro-N-[2-(3,4-dichloro-phenyl)-1-(4-fluoro-benzylcarbamoyl)-ethyl]-benzamideYield 46%

Procedure

The title compound (27 mg, 46%) was obtained from (S)-2-[2-(benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-chloro-benzoylamino]-3-(3,4-dichloro-phenyl)-propionic acid and 4-fluorobenzyl amine as in Example 1, Part C. HPLC: RT=10.66 min. MS (ESI−): mass calcd. for C29H21Cl3FN5O4S2, 693.00; m/z found, 690/692 [M−H]−. 1H NMR (500 MHz, CDCl3): 11.55 (s, 1H), 8.38 (dd, J=7.0, 0.8, 1H), 8.21 (dd, J=8.8, 0.6, 1H), 7.72 (dd, J=8.8, 7.1, 1H), 7.68 (d, J=1.9, 1H), 7.35-7.32 (m, 1H), 7.30-7.25 (m, 2H), 7.12-7.07 (m, 2H), 7.05-6.99 (m, 5H), 6.94 (dd, J=8.4, 1.9, 1H), 6.88-6.81 (m, 1H), 5.79-5.72 (m, 1H), 4.67-4.59 (m, 1H), 4.47-4.40 (m,1H), 4.29-4.25 (m, 1H), 3.15-3.11 (m, 1H), 3.00-2.96 (m, 1H).

Sources & evidence

ORD record
ord-c0c9741c06ab43478f36964f5f10f4bd
Source dataset
uspto-grants-2007_11
Patent number
US07297816B2

Reaction notes

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