Potassium Carbonate → HCID 178499564, compound

HRID 705885Notes

Reaction equation

[C:1](=[NH:24])([O:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([C:20]([F:23])([F:22])[F:21])[CH:14]=2)=[CH:8][CH:7]=1)[NH2:2].[CH:25]([CH:27]([CH2:32][C:33]([O:35][CH3:36])=[O:34])[C:28](OC)=O)=[O:26].C([O-])([O-])=O.[K+].[K+]>CN1C(=O)CCC1>[Cl:19][C:16]1[CH:17]=[CH:18][C:13]([O:12][C:9]2[CH:8]=[CH:7][C:6]([CH2:5][CH2:4][O:3][C:1]3[NH:2][CH:28]=[C:27]([CH2:32][C:33]([O:35][CH3:36])=[O:34])[C:25](=[O:26])[N:24]=3)=[CH:11][CH:10]=2)=[CH:14][C:15]=1[C:20]([F:23])([F:22])[F:21]

Participants

Conditions

Temperature: 130 °C

Procedure

To a solution of 2-(4-{[4-chloro-3-(trifluoromethyl)phenyl]oxy}phenyl)ethyl imidocarbamate (437 mg, 0.861 mmol) and dimethyl 2-formylbutanedioate (450 mg, 2.58 mmol) in NMP (5 mL) was added K2CO3 (357 mg, 2.58 mmol). The mixture was heated at 130° C. for 1.5 h. Purification via reverse phase flash chromatography then afforded the title compound, together with ethyl ester (102 mg, 0.211 mmol, 24.55% yield).

Workup

customPurification via reverse phase flash chromatography

Sources & evidence

ORD record: ord-04753acd16be4471a58733caa210464f
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09174968B2

Reaction notes

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