Diisopropylethylamine → Methyl 4-[({[trans-4-(2,4-dichlorophenyl)-5-nitrocyclohex-1-en-1-yl]methyl}amino)carbonyl]benzoate

HRID 1172335Notes

Reaction equation

HRID 1172335 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C@H:9]1[C@H:14]([N+:15]([O-:17])=[O:16])[CH2:13][C:12]([CH2:18][NH2:19])=[CH:11][CH2:10]1.[CH3:20][O:21][C:22](=[O:32])[C:23]1[CH:28]=[CH:27][C:26]([C:29](Cl)=[O:30])=[CH:25][CH:24]=1.C(N(C(C)C)CC)(C)C>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C@H:9]1[C@H:14]([N+:15]([O-:17])=[O:16])[CH2:13][C:12]([CH2:18][NH:19][C:29]([C:26]2[CH:27]=[CH:28][C:23]([C:22]([O:21][CH3:20])=[O:32])=[CH:24][CH:25]=2)=[O:30])=[CH:11][CH2:10]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 81850Methyl 4-(chlorocarbonyl)benzoateHCID 68769505[trans-4-(2,4-Dichlorophenyl)-5-nitrocyclohex-1-en-1-yl]methyl amine

Product 1

HCID 68770735Methyl 4-[({[trans-4-(2,4-dichlorophenyl)-5-nitrocyclohex-1-en-1-yl]methyl}amino)carbonyl]benzoateYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Example 12C (33 mg, 0.11 mmol) in CH2Cl2 (1 mL), 4-chlorocarbonyl-benzoic acid methyl ester (33 mg, 0.16 mmol) and diisopropylethyl amine (0.05 mL, 0.33 mmol) were added. The reaction mixture was stirred at room temperature overnight. It was 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 (41 mg, 81%). 1H NMR (500 MHz, CDCL3) δ ppm 8.06-8.10 (m, 2H), 7.86-7.92 (m, 2H), 7.37-7.41 (m, 1H), 7.15-7.26 (m, 2H), 5.73-5.82 (m, 1H), 5.02-5.13 (m, 1H), 4.01-4.13 (m, 3H), 2.50-2.95 (m, 3H). MS (ESI) m/z 463 (M+H)+.

Workup

  1. concentrationIt was concentrated under reduced pressure
  2. custompurified by high pressure liquid chromotography (eluting with 0-70% acetonitrile/water and 0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-b40c194942214c6893b3d9a15e348837
Source dataset
uspto-grants-2010_11
Patent number
US07834012B2

Reaction notes

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