Potassium Fluoride → 3-{3-Cyano-6-[(2,2-dimethyl-propyl)-amino]-5-fluoro-pyridin-2-ylamino}-N-methoxy-4-methyl-benzamide

HRID 1666066Notes

Reaction equation

Cl[C:2]1[N:9]=[C:8]([NH:10][CH2:11][C:12]([CH3:15])([CH3:14])[CH3:13])[C:7]([F:16])=[CH:6][C:3]=1[C:4]#[N:5].[NH2:17][C:18]1[CH:19]=[C:20]([CH:26]=[CH:27][C:28]=1[CH3:29])[C:21]([NH:23][O:24][CH3:25])=[O:22].[F-].[K+]>CS(C)=O>[C:4]([C:3]1[C:2]([NH:17][C:18]2[CH:19]=[C:20]([CH:26]=[CH:27][C:28]=2[CH3:29])[C:21]([NH:23][O:24][CH3:25])=[O:22])=[N:9][C:8]([NH:10][CH2:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[C:7]([F:16])[CH:6]=1)#[N:5]

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 2-chloro-6-[(2,2-dimethyl-propyl)-amino]-5-fluoro-nicotinonitrile (150 mg, 0.62 mmol), 3-amino-N-methoxy-4-methyl-benzamide (150 mg, 0.83 mmol) and potassium fluoride (30 mg, 0.51 mmol) in DMSO (1 mL) was heated to 150° C. overnight. The reaction mixture was allowed to cool to room temp and then partitioned between water and ethyl acetate. The organic layer was dried (sodium sulfate) and concentrated under reduced pressure. The product (2.5 mg, 1%) was obtained after purification by silica gel chromatography with 30% EtOAc in hexane as eluent. C20H24FN5O2 MS m/e=386 (M+H).

Workup

temperatureto cool to room temp
custompartitioned between water and ethyl acetate
dry with materialThe organic layer was dried (sodium sulfate)
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-a2f9e6e992e6404195f9334ff60cb11b
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08044040B2

Reaction notes

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