Acetic Acid → 4-chloro-N-(6-(4-cyclopropyl-4H-1,2,4-triazol-3-yl)pyridin-2-yl)picolinamide

HRID 1040240

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([NH:19][NH2:20])=O)[N:12]=2)=[O:9])[CH:3]=1.[CH:21]1([NH2:24])[CH2:23][CH2:22]1.[C:25](O)(=O)C>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]3[N:24]([CH:21]4[CH2:23][CH2:22]4)[CH:25]=[N:20][N:19]=3)[N:12]=2)=[O:9])[CH:3]=1

Participants

Conditions

Temperature: 150 °C

Procedure

To a suspension of 4-chloro-N-(6-(hydrazinecarbonyl)pyridin-2-yl)picolinamide (1.00 g, 3.43 mmol) in toluene (0.20 M) was added a mixture of N,N-dimethylformamide•N-dimethylacetamide (1.14 mL, 8.56 mmol), cyclopropylamine (873 μL, 13.7 mmol), and acetic acid (194 μL, 3.43 mmol). The reaction mixture was heated to 150° C. for 30 minutes in a microwave reactor. The reaction product was concentrated under reduced pressure, and the residue was suspended in acetonitrile/diethylether (1.5 mL, 1:1 ratio), filtered, and the solid washed with acetonitrile/diethylether (2×10 mL). The filtrate was concentrated and the solid thus obtained was purified as above. The combined solids were dried under reduced pressure to afford 842 mg (72% yield) of 4-chloro-N-(6-(4-cyclopropyl-4H-1,2,4-triazol-3-yl)pyridin-2-yl)picolinamide as a white solid.

Workup

additionwas added
concentrationThe reaction product was concentrated under reduced pressure
filtrationfiltered
washthe solid washed with acetonitrile/diethylether (2×10 mL)
concentrationThe filtrate was concentrated
customthe solid thus obtained
customwas purified as above
customThe combined solids were dried under reduced pressure

Sources & evidence

ORD record: ord-60701079064d426aae184b9f1c85e53f
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08552196B2

Linked notes

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