Potassium Carbonate → HCID 178525670, compound

HRID 474790Notes

Reaction equation

[C:1](=[NH:25])([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)=[C:8]([F:24])[CH:7]=1)[NH2:2].[OH:26]/[CH:27]=[C:28](/[CH2:33][C:34]1[CH:35]=[N:36][CH:37]=[N:38][CH:39]=1)\[C:29](OC)=O.[C:40]([O-:43])([O-])=[O:41].[K+].[K+]>CN1C(=O)CCC1>[F:21][C:20]([F:23])([F:22])[C:40]([OH:43])=[O:41].[Cl:19][C:16]1[CH:17]=[CH:18][C:13]([O:12][C:9]2[CH:10]=[CH:11][C:6]([CH2:5][CH2:4][O:3][C:1]3[NH:2][CH:29]=[C:28]([CH2:33][C:34]4[CH:39]=[N:38][CH:37]=[N:36][CH:35]=4)[C:27](=[O:26])[N:25]=3)=[CH:7][C:8]=2[F:24])=[CH:14][C:15]=1[C:20]([F:23])([F:21])[F:22]

Participants

Conditions

Temperature: 160 °C

Procedure

The mixture of 2-(4-{[4-chloro-3-(trifluoromethyl)phenyl]oxy}-3-fluorophenyl)ethyl imidocarbamate (200 mg, 0.380 mmol), methyl (2Z)-3-hydroxy-2-(5-pyrimidinylmethyl)-2-propenoate (147 mg, 0.759 mmol) and K2CO3 (105 mg, 0.759 mmol) in NMP (5 mL) was heated with a microwave reactor at 160° C. for 1.5 h. Purification via MDAP then afforded the title compound (100 mg, 41.5% yield). LCMS: rt=3.42 min, [M+H+]=521

Workup

customPurification via MDAP

Sources & evidence

ORD record: ord-dd31c15227d445f2a2ba407a8d243aee
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637536B2

Reaction notes

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