1,2-Dichloroethane → HCID 9915927, compound

HRID 2187614Notes

Reaction equation

HRID 2187614 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:15][C:16]2[CH:24]=[CH:23][C:19]([C:20]([OH:22])=O)=[C:18]([C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)[CH:17]=2)[CH2:9][N:10]2[CH:14]=[CH:13][N:12]=[CH:11]2)=[CH:4][CH:3]=1.[NH2:32][C@@H:33]([CH2:38][CH2:39][S:40][CH3:41])[C:34]([O:36][CH3:37])=[O:35].Cl.COC(=O)[C@H](CCSC)N.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C1C=CN=CC=1)C.ClCCl>[F:31][C:28]1[CH:27]=[CH:26][C:25]([C:18]2[CH:17]=[C:16]([NH:15][CH:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[CH2:9][N:10]3[CH:14]=[CH:13][N:12]=[CH:11]3)[CH:24]=[CH:23][C:19]=2[C:20]([NH:32][C@@H:33]([CH2:38][CH2:39][S:40][CH3:41])[C:34]([O:36][CH3:37])=[O:35])=[O:22])=[CH:30][CH:29]=1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 64684methyl (2S)-2-amino-4-(methylsulfanyl)butanoateHCID 757711-HydroxybenzotriazoleHCID 110802754-{1-(4-Fluorophenyl)-2-(imidazol-1-yl)ethylamino]-2-(4-fluorophenyl)benzoic acidHCID 11435579L-Methionine, methyl ester, hydrochloride

Product 1

HCID 9915927HCID 9915927, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 4-{1-(4-fluorophenyl)-2-(imidazol-1-yl)ethylamino]-2-(4-fluorophenyl)benzoic acid (1.67 g; 4 mmol), methyl (2S)-2-amino-4-(methylsulfanyl)butanoate, (L-methionine methyl ester hydrochloride) (0.96 g; 4.8 mmol), HOBT (0.65 g; 4.8 mmol), EDC (0.925 g; 4.8 mmol) and DMAP (0.54 g; 4.4 mmol) in dichloromethane (100 ml) was stirred at ambient temperature for 5 hours. The solution was diluted with dichloromethane (200 ml), washed with 5% aqueous sodium hydrogen carbonate solution and evaporated to dryness. The residue was purified by flash chromatography eluting with dichloromethane/ethanol 95/5 to give the title compound as a solid (1.8 g; 80%).

Workup

  1. washwashed with 5% aqueous sodium hydrogen carbonate solution
  2. customevaporated to dryness
  3. customThe residue was purified by flash chromatography
  4. washeluting with dichloromethane/ethanol 95/5

Sources & evidence

ORD record
ord-8854e22cd67643c2ac15bfd2a87f9261
Source dataset
uspto-grants-2002_06
Patent number
US06410539B1

Reaction notes

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