Piperidine → (S)-2-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-chloro-N-[1-(3,4-dichloro-benzyl)-2-oxo-2-piperidin-1-yl-ethyl]-benzamide

HRID 2265285Notes

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.[NH:37]1[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]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]([CH2:23][C:24]3[CH:29]=[CH:28][C:27]([Cl:30])=[C:26]([Cl:31])[CH:25]=3)[C:20](=[O:21])[N:37]3[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]3)=[O:17])(=[O:12])=[O:11])=[CH:7][CH:8]=[CH:9][C:2]=12

Participants

Reactant 2

HCID 8082Piperidine

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 58999916(S)-2-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-chloro-N-[1-(3,4-dichloro-benzyl)-2-oxo-2-piperidin-1-yl-ethyl]-benzamideYield 66%

Procedure

The title compound (37 mg, 66%) was prepared from (S)-2-[2-(benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-chloro-benzoylamino]-3-(3,4-dichloro-phenyl)-propionic acid and piperidine as in Example 1, Part C. HPLC: RT=11.00 min. MS (ESI−): mass calcd. for C27H24Cl3N5O4S2, 653.00; m/z found, 650/652 [M−H]−. 1H NMR (500 MHz, CDCl3): 11.70 (m, 1H), 8.38 (d, J=7.0, 1H), 8.21 (d, J=8.8, 1H), 7.72 (dd, J=8.8, 7.1, 1H), 7.69 (d, J=1.9, 1H), 7.35 (d, J=8.2, 1H), 7.28-7.25 (m, 1H), 7.22 (d, J=1.9, 1H), 7.13 (d, J=7.4, 1H), 6.99 (dd, J=8.2, 1.9, 1H), 6.92 (dd, J=8.4, 1.9, 1H), 5.26-5.21 (m, 1H), 3.62-3.49 (m, 2H), 3.43-3.35 (m, 1H), 3.26-3.19 (m, 1H), 3.08-2.95 (m, 2H), 1.70-1.46 (m, 5H), 1.33-1.23 (m, 1H).

Sources & evidence

ORD record: ord-2bb05a9bf0934c28a44598e9c8434e14
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07855292B2

Reaction notes

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