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

HRID 563645Notes

Reaction equation

HRID 563645 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-7e43308dc2ee4bff9fe032b1d8ea6803
Source dataset
uspto-grants-2011_11
Patent number
US08067445B2

Reaction notes

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