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

HRID 852021Notes

Reaction equation

Cl[C:2]1[N:9]=[C:8]([N:10]([CH2:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH3:11])[C:7]([F:17])=[CH:6][C:3]=1[C:4]#[N:5].[NH2:18][C:19]1[CH:20]=[C:21]([CH:27]=[CH:28][C:29]=1[CH3:30])[C:22]([NH:24][O:25][CH3:26])=[O:23].[F-].[K+]>CS(C)=O>[C:4]([C:3]1[C:2]([NH:18][C:19]2[CH:20]=[C:21]([CH:27]=[CH:28][C:29]=2[CH3:30])[C:22]([NH:24][O:25][CH3:26])=[O:23])=[N:9][C:8]([N:10]([CH2:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH3:11])=[C:7]([F:17])[CH:6]=1)#[N:5]

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 2-chloro-6-[(2,2-dimethyl-propyl)-methyl-amino]-5-fluoro-nicotinonitrile (120 mg, 0.47 mmol), 3-amino-N-methoxy-4-methyl-benzamide (120 mg, 0.66 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 down 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 (7.5 mg, 4%) was obtained after purification by silica gel chromatography with 30% EtOAc in hexane as eluent. C21H26FN5O2 MS m/e=400 (M+H).

Workup

temperatureto cool down 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-47ee16705e2e4c918cfa60996e361470
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07253174B2

Reaction notes

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