Triethylamine → 2'-Chloro-5'-(3-cyclohexyl-ureido)-biphenyl-4-carboxylic acid ethyl ester

HRID 1678520Notes

Reaction equation

HRID 1678520 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[C:16]([NH2:18])[CH:15]=[CH:14][C:13]=2[Cl:19])=[CH:8][CH:7]=1)=[O:5])[CH3:2].[CH:20]1([N:26]=[C:27]=[O:28])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1.C(N(CC)CC)C>C1COCC1>[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[C:16]([NH:18][C:27]([NH:26][CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)=[O:28])[CH:15]=[CH:14][C:13]=2[Cl:19])=[CH:8][CH:7]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 18502Cyclohexyl isocyanateHCID 598223745'-Amino-2'-chloro-biphenyl-4-carboxylic acid ethyl ester

Product 1

HCID 673754852'-Chloro-5'-(3-cyclohexyl-ureido)-biphenyl-4-carboxylic acid ethyl esterYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5′-amino-2′-chloro-biphenyl-4-carboxylic acid ethyl ester (350 mg) and cyclohexyl isocyanate (0.32 ml) in dry THF (15 ml) containing triethylamine (0.62 ml) was stirred at room temp for 48 h. The mixture was then evaporated and the residue partitioned between water and DCM. The dried extracts were evaporated giving the crude title compound as a white solid (616 mg, >100%, contaminated with dicyclohexyl-urea)

Workup

  1. customThe mixture was then evaporated
  2. customthe residue partitioned between water and DCM
  3. customThe dried extracts were evaporated

Sources & evidence

ORD record
ord-db375e4ce321484687619e31dc600eb1
Source dataset
uspto-grants-2011_08
Patent number
US08008303B2

Reaction notes

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