Cesium carbonate → HCID 178518461, compound

HRID 706091Notes

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]([O:20][C:21]([F:24])([F:23])[F:22])[CH:14]=2)=[CH:8][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([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1>[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: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:11][CH:10]=2)=[CH:14][C:15]=1[O:20][C:21]([F:24])([F:22])[F:23]

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 4-(4-chloro-3-(trifluoromethoxy)phenoxy)phenethyl carbamimidate (80 mg, 0.213 mmol), (Z)-methyl 3-hydroxy-2-(pyrimidin-5-ylmethyl)acrylate (124 mg, 0.640 mmol) and Cs2CO3 (174 mg, 0.534 mmol) in 1,4-dioxane (2 mL) was heated with a microwave condition at 110° C. for 2 h. After cooling, the mixture was filtered through the celite. The filtrate was concentrated and purified via reverse phase flash chromatography to afford the title compound (48 mg, 0.093 mmol, 43.3% yield). LCMS: rt=3.48 min, [M+H+]=519

Workup

temperatureAfter cooling
filtrationthe mixture was filtered through the celite
concentrationThe filtrate was concentrated
custompurified via reverse phase flash chromatography

Sources & evidence

ORD record: ord-8ed6f4a9ff6849ef85da4764ed064672
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09174968B2

Reaction notes

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