Phosgene → {2'-[3-(4-Chloro-benzyl)-1-ethyl-ureidomethyl]-4'-fluoro-6-methoxy-biphenyl-3-yl}-acetic acid ethyl ester

HRID 1810454Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:25])[CH2:5][C:6]1[CH:7]=[C:8]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=2[CH2:21][NH:22][CH2:23][CH3:24])[C:9]([O:12][CH3:13])=[CH:10][CH:11]=1)[CH3:2].C(N(C(C)C)CC)(C)C.[C:35](Cl)(Cl)=[O:36].[Cl:39][C:40]1[CH:47]=[CH:46][C:43]([CH2:44][NH2:45])=[CH:42][CH:41]=1>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:25])[CH2:5][C:6]1[CH:7]=[C:8]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=2[CH2:21][N:22]([CH2:23][CH3:24])[C:35]([NH:45][CH2:44][C:43]2[CH:46]=[CH:47][C:40]([Cl:39])=[CH:41][CH:42]=2)=[O:36])[C:9]([O:12][CH3:13])=[CH:10][CH:11]=1)[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

(2′-Ethylaminomethyl-4′-fluoro-6-methoxy-biphenyl-3-yl)-acetic acid ethyl ester (0.172 g, 0.5 mmol) and diisopropylethylamine (0.43 mL, 2.5 mmol) were combined in CH2Cl2 (2.5 mL) and cooled to 0° C. Phosgene (20% in toluene; 0.40 mL, 0.75 mmol) was added, and the mixture was stirred for 1 hour. 4-Chlorobenzylamine (0.012 mL, 1.0 mmol) was added, and the reaction was stirred for 1 hour. The mixture was diluted with CH2Cl2 and washed with H2O. The organic layer was dried, filtered, and concentrated, and the residue was purified by preparative HPLC to give the title compound.

Workup

stirringthe reaction was stirred for 1 hour
washwashed with H2O
customThe organic layer was dried
filtrationfiltered
concentrationconcentrated
customthe residue was purified by preparative HPLC

Sources & evidence

ORD record: ord-bb5937b41867423385e0ac955736caee
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08362044B2

Reaction notes

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