Triethylamine → {2'-[3-(3,4-Dichloro-benzyl)-1-ethyl-ureidomethyl]-6-methoxy-4'-trifluoromethyl-biphenyl-3-yl}-acetic acid ethyl ester

HRID 2197355Notes

Reaction equation

HRID 2197355 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].C(N(CC)CC)C.[Cl:36][C:37]1[CH:38]=[C:39]([CH:44]=[CH:45][C:46]=1[Cl:47])[CH2:40][N:41]=[C:42]=[O:43]>C(Cl)Cl>[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:42]([NH:41][CH2:40][C:39]2[CH:44]=[CH:45][C:46]([Cl:47])=[C:37]([Cl:36])[CH:38]=2)=[O:43])[C:9]([O:12][CH3:13])=[CH:10][CH:11]=1)[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27333681,2-Dichloro-4-(isocyanatomethyl)benzeneHCID 66604101(2'-Ethylaminomethyl-6-methoxy-4'-trifluoromethyl-biphenyl-3-yl)-acetic acid ethyl ester

Product 1

HCID 66604343{2'-[3-(3,4-Dichloro-benzyl)-1-ethyl-ureidomethyl]-6-methoxy-4'-trifluoromethyl-biphenyl-3-yl}-acetic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(2′-Ethylaminomethyl-6-methoxy-4′-trifluoromethyl-biphenyl-3-yl)-acetic acid ethyl ester (0.170 g, 0.42 mmol) and triethylamine (0.12 mL, 0.86 mmol) were combined in CH2Cl2 (2 mL). 3,4-Dichlorobenzyl isocyanate (0.08 mL, 0.52 mmol) was added, and the reaction was stirred at room temperature for 15 minutes. After concentrating, the crude material was purified by silica gel chromatography (20-50% EtOAc in hexanes) to give {2′-[3-(3,4-dichloro-benzyl)-1-ethyl-ureidomethyl]-6-methoxy-4′-trifluoromethyl-biphenyl-3-yl}-acetic acid ethyl ester. The ethyl ester was hydrolyzed according to the procedure described in Example 23, Step 2.

Workup

  1. concentrationAfter concentrating
  2. customthe crude material was purified by silica gel chromatography (20-50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-5308d3b2ebc94a78ae9ec880eb84b401
Source dataset
uspto-grants-2012_12
Patent number
US08338484B2

Reaction notes

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