Triethylamine → 3-(3-Cyano-6-chloro-5-fluoro-pyridin-2-ylamino)-N-methoxy-4-methyl-benzamide

HRID 1666069Notes

Reaction equation

Cl[C:2]1[N:9]=[C:8]([Cl:10])[C:7]([F:11])=[CH:6][C:3]=1[C:4]#[N:5].[NH2:12][C:13]1[CH:14]=[C:15]([CH:21]=[CH:22][C:23]=1[CH3:24])[C:16]([NH:18][O:19][CH3:20])=[O:17].C(N(CC)CC)C>C(#N)C>[C:4]([C:3]1[C:2]([NH:12][C:13]2[CH:14]=[C:15]([CH:21]=[CH:22][C:23]=2[CH3:24])[C:16]([NH:18][O:19][CH3:20])=[O:17])=[N:9][C:8]([Cl:10])=[C:7]([F:11])[CH:6]=1)#[N:5]

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 2,6-dichloro-5-fluoro-nicotinonitrile (830 mg, 4.34 mmol), 3-amino-N-methoxy-4-methyl-benzamide (576 mg, 3.2 mmol) and triethylamine (0.5 mL) in acetonitrile (10 mL) was heated to 70° C. overnight. Then the solvent was removed under reduced pressure and the reaction mixture was partitioned between water and ethyl acetate. The organic layer was dried (sodium sulfate) and concentrated under reduced pressure. The product (220 mg, 21%) was isolated after purification by silica gel chromatography. C15H12ClFN4O2 MS m/e=335 (M+H).

Workup

customThen the solvent was removed under reduced pressure
customthe reaction mixture was partitioned between water and ethyl acetate
dry with materialThe organic layer was dried (sodium sulfate)
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-e1a90b48b8c34391abc6b77bd1712b7c
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08044040B2

Reaction notes

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