1,2-Dichloroethane → HCID 11349980, compound

HRID 1766425Notes

Reaction equation

HRID 1766425 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[F:29])[C:10]([CH2:16][NH:17][CH:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)=[C:11]([C:13](O)=[O:14])[N:12]=2)=[CH:4][CH:3]=1.C(Cl)CCl.C1C=NC2N(O)N=NC=2C=1.C(N(CC)CC)C>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[F:29])[C:10]3[CH2:16][N:17]([CH:18]4[CH2:19][CH2:20][CH2:21][CH2:22]4)[C:13](=[O:14])[C:11]=3[N:12]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 181649HOAtHCID 21868784HCID 21868784, compound

Product 1

HCID 11349980HCID 11349980, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-(4-chloro-phenyl-5-cyclopentylaminomethyl-1-(2-fluoro-phenyl)-1H-imidazole-4-carboxylic acid I-5 k (1.2 g, 2.59 mmol), EDC (994 mg, 5.18 mmol), HOAt (704 mg, 5.18 mmol), and triethylamine (1.1 ml, 7.76 mmol) in CH2Cl2 (200 ml) was stirred for 17 hours at room temperature. The reaction mixture was washed with sat'd aq NaHCO3 and sat'd aq. NaCl, dried and concentrated in vacuo. The crude residue was purified on SiO2-gel using a solvent gradient of 30% EtOAc/hexanes to 60% EtOAc/hexanes to give 4A-1 as a white solid (752 mg, 73%): +APCI MS (M+1) 396.2; 1H NMR (CDCl3): δ 7.61-7.59 (m, 2H), 7.42-7.37 (m, 6H), 4.60 (m, 1H), 4.50 (s, 2H), 2.0 (m, 2H), 1.8-1.65 (m, 6H).

Workup

  1. washThe reaction mixture was washed with sat'd aq NaHCO3
  2. customdried
  3. concentrationconcentrated in vacuo
  4. customThe crude residue was purified on SiO2-gel

Sources & evidence

ORD record
ord-9b17e5060a4d44b1b9944ccb60a333eb
Source dataset
uspto-grants-2007_06
Patent number
US07230024B2

Reaction notes

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