Dimethylformamide → HCID 70815699, compound

HRID 1843042Notes

Reaction equation

[Cl:1][C:2]1[CH:11]=[C:10]([NH:12][C:13]([O:15]C2C=CC=CC=2)=O)[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[Cl:22][C:23]1[CH:24]=[C:25]([N:29]2[C:33](CN)=[CH:32][C:31]([C:36]([F:39])([F:38])[F:37])=[N:30]2)[CH:26]=[CH:27][CH:28]=1.[CH3:40][N:41](C=O)C>CN(C1C=CN=CC=1)C>[CH3:7][O:6][C:4](=[O:5])[C:3]1[CH:8]=[CH:9][C:10]([NH:12][C:13](=[O:15])[N:41]([C:33]2[N:29]([C:25]3[CH:26]=[CH:27][CH:28]=[C:23]([Cl:22])[CH:24]=3)[N:30]=[C:31]([C:36]([F:37])([F:38])[F:39])[CH:32]=2)[CH3:40])=[CH:11][C:2]=1[Cl:1]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of methyl 2-chloro-4-(phenoxycarbonylamino)benzoate (80 mg, 0.26 mmol) in DMF was added DMAP (32 mg, 0.26 mmol) and (1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methanamine (74 mg, 0.27 mmol) at room temperature. The reaction mixture was heated to 50° C. overnight. TLC showed complete consumption of starting material. The reaction mixture was diluted with water and extracted with EtOAc. The organic layer was washed with water and brine. The organic layer was dried over MgSO4 and concentrated under reduced pressure. The crude product was purified by column chromatography to give pure example compound E59 (77 mg).

Workup

customconsumption of starting material
additionThe reaction mixture was diluted with water
extractionextracted with EtOAc
washThe organic layer was washed with water and brine
dry with materialThe organic layer was dried over MgSO4
concentrationconcentrated under reduced pressure
customThe crude product was purified by column chromatography
customto give pure example compound

Sources & evidence

ORD record: ord-c618c602aa184cb5ba192528aeae6698
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946204B2

Reaction notes

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