3-Chloro-n-{[trans-4-(2,4-dichlorophenyl)-5-nitrocyclohex-1-en-1-yl]methyl}-4-(methylsulfonyl)thiophene-2-carboxamide → n-{[trans-5-Amino-4-(2,4-dichlorophenyl)cyclohex-1-en-1-yl]methyl}-3-chloro-4-(methylsulfonyl)thiophene-2-carboxamide

HRID 1172333Notes

Reaction equation

HRID 1172333 reaction equation
[Cl:1][C:2]1[C:6]([S:7]([CH3:10])(=[O:9])=[O:8])=[CH:5][S:4][C:3]=1[C:11]([NH:13][CH2:14][C:15]1[CH2:20][C@@H:19]([N+:21]([O-])=O)[C@H:18]([C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][C:25]=2[Cl:31])[CH2:17][CH:16]=1)=[O:12]>[Zn].CO.C(O)(=O)C>[NH2:21][C@@H:19]1[CH2:20][C:15]([CH2:14][NH:13][C:11]([C:3]2[S:4][CH:5]=[C:6]([S:7]([CH3:10])(=[O:9])=[O:8])[C:2]=2[Cl:1])=[O:12])=[CH:16][CH2:17][C@H:18]1[C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][C:25]=1[Cl:31]

Participants

4

Reactant 1

HCID 687719313-Chloro-n-{[trans-4-(2,4-dichlorophenyl)-5-nitrocyclohex-1-en-1-yl]methyl}-4-(methylsulfonyl)thiophene-2-carboxamide

Product 1

HCID 68770383n-{[trans-5-Amino-4-(2,4-dichlorophenyl)cyclohex-1-en-1-yl]methyl}-3-chloro-4-(methylsulfonyl)thiophene-2-carboxamideYield 66%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 10129899Acetic acid methanolSolvent

Procedure

To a solution of Example 12D (40 mg, 0.077 mmol) in mixture of methanol/acetic acid (0.5 mL/0.5 mL), Zn powder (50 mg, 0.77 mmol) was added at room temperature. The reaction mixture was stirred for thirty minutes, filtered, concentrated under reduced pressure, and purified by high pressure liquid chromotography (eluting with 0-70% acetonitrile/water and 0.1% trifluoroacetic acid) to provide the title compound (25 mg, 66%). 1H NMR (400 MHz, methanol-d4) δ ppm 8.45 (s, 1H), 8.03 (s, 1H), 7.54 (s, 1H), 7.35-7.47 (m, 2H), 5.82 (m, 1H), 3.82-4.06 (m, 3H), 3.49-3.61 (m, 1H), 3.18 (s, 3H), 2.43-2.62 (m, 2H), 2.24-2.42 (m, 2H). MS (ESI) m/z 493 (M+H)+.

Workup

  1. additionwas added at room temperature
  2. filtrationfiltered
  3. concentrationconcentrated under reduced pressure
  4. custompurified by high pressure liquid chromotography (eluting with 0-70% acetonitrile/water and 0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-6ac43cbadbb745ed930ec587cfec67ed
Source dataset
uspto-grants-2010_11
Patent number
US07834012B2

Reaction notes

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