1,2-Dichloroethane → HCID 178458111, compound

HRID 333431Notes

Reaction equation

HRID 333431 reaction equation
[NH:1]1[CH:5]=[C:4]([CH2:6][CH2:7][NH:8][C:9](=[O:24])[NH:10][CH:11]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[C:12]([OH:14])=O)[N:3]=[CH:2]1.[F:25][C:26]([F:31])([F:30])[C:27]([OH:29])=[O:28].[CH3:32][CH:33]1[CH2:38][CH2:37][CH2:36][CH2:35][CH:34]1[C:39]1([O:43][CH2:44][CH2:45][CH3:46])[CH2:42][NH:41][CH2:40]1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[OH-].[Na+]>CN(C=O)C>[F:25][C:26]([F:31])([F:30])[C:27]([OH:29])=[O:28].[NH:1]1[CH:5]=[C:4]([CH2:6][CH2:7][NH:8][C:9]([NH:10][CH:11]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[C:12]([N:41]2[CH2:40][C:39]([CH:34]3[CH2:35][CH2:36][CH2:37][CH2:38][CH:33]3[CH3:32])([O:43][CH2:44][CH2:45][CH3:46])[CH2:42]2)=[O:14])=[O:24])[N:3]=[CH:2]1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 14798Sodium HydroxideHCID 757711-HydroxybenzotriazoleHCID 66988243HCID 66988243, compoundHCID 178490381HCID 178490381, compound

Product 1

HCID 178458111HCID 178458111, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 97 mg (0.29 mmol) of 2-{3-[2-(1H-imidazol-4-yl)ethyl]ureido}-3-(4-methoxyphenyl)-propanoic acid (cf. preparation 2-3) dissolved in 2 mL of DMF are added 94 mg (0.29 mmol) of 3-(2-methylcyclohexyl)-3-propoxyazetidine trifluoroacetate, 70 mg (0.37 mmol) of EDC and 45 mg (0.33 mmol) of HOBt. After 3 hours, the reaction medium is hydrolysed with aqueous 1N sodium hydroxide solution and then extracted with dichloromethane. The organic phase is dried over MgSO4, filtered and concentrated. The crude product obtained is purified by preparative HPLC. 33 mg of 1-[2-(1H-imidazol-4-yl)ethyl]-3-{1-(4-methoxybenzyl)-2-[3-(2-methylcyclohexyl)-3-propoxyazetidin-1-yl]-2-oxoethyl}urea trifluoroacetate are obtained in a yield of 18%.

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe organic phase is dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product obtained
  6. customis purified by preparative HPLC

Sources & evidence

ORD record
ord-c4b4663ad34a47b38f2e3982ddea94e3
Source dataset
uspto-grants-2014_11
Patent number
US08877968B2

Reaction notes

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