Acetic Acid → {2'-[(1-Ethyl-ureido)-methyl]-6-methoxy-4'-trifluoromethyl-biphenyl-3-yl}-acetic acid ethyl ester

HRID 1810407Notes

Reaction equation

HRID 1810407 reaction equation
[CH2:1]([O:3][C:4](=[O:28])[CH2:5][C:6]1[CH:7]=[C:8]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][C:15]=2[CH2:24][NH:25][CH2:26][CH3:27])[C:9]([O:12][CH3:13])=[CH:10][CH:11]=1)[CH3:2].[O-:29][C:30]#[N:31].[Na+].C(O)(=O)C.CN(C=O)C>O>[CH2:1]([O:3][C:4](=[O:28])[CH2:5][C:6]1[CH:7]=[C:8]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:21])[F:22])=[CH:16][C:15]=2[CH2:24][N:25]([CH2:26][CH3:27])[C:30]([NH2:31])=[O:29])[C:9]([O:12][CH3:13])=[CH:10][CH:11]=1)[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6228DimethylformamideHCID 517096Sodium CyanateHCID 66604101(2'-Ethylaminomethyl-6-methoxy-4'-trifluoromethyl-biphenyl-3-yl)-acetic acid ethyl ester

Product 1

HCID 66607402{2'-[(1-Ethyl-ureido)-methyl]-6-methoxy-4'-trifluoromethyl-biphenyl-3-yl}-acetic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(2′-Ethylaminomethyl-6-methoxy-4′-trifluoromethyl-biphenyl-3-yl)-acetic acid ethyl ester (0.202 g, 0.51 mmol) and sodium cyanate (0.052 g, 0.77 mmol) were combined in H2O (2 mL). Acetic acid (0.04 mL, 0.77 mmol) was added, and the reaction was stirred for 1 hour. DMF (1 mL) was added to facilitate stirring, and the reaction was stirred for 1.5 hours. The solution was extracted with EtOAc, and the combined organic layers were dried and concentrated to give the title compound.

Workup

  1. stirringto facilitate stirring
  2. stirringthe reaction was stirred for 1.5 hours
  3. extractionThe solution was extracted with EtOAc
  4. customthe combined organic layers were dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e84ab661f3a64f5184baf5df52b8187b
Source dataset
uspto-grants-2013_01
Patent number
US08362044B2

Reaction notes

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