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

HRID 852024Notes

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-921d65de7d6d41819cd1b2b6f6c98de3
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07253174B2

Reaction notes

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