Ethyl 4,6-dichloropyridazine-3-carboxylate → ethyl 4-(6-(2H-1,2,3-triazol-2-yl)pyridin-2-ylamino)-6-chloropyridazine-3-carboxylate

HRID 1396409Notes

Reaction equation

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

Participants

Conditions

Temperature: 140 °C

Procedure

To a solution of ethyl 4,6-dichloropyridazine-3-carboxylate (154 mg, 695 μmol) in acetonitrile was added 6-(2H-1,2,3-triazol-2-yl)pyridin-2-amine (112 mg, 695 μmol) and heated to 140° C. for 72 h. The mixture was cooled and precipitated by addition of acetone. The mixture was filtered and the solid collected was washed with methanol and ether then dried to give ethyl 4-(6-(2H-1,2,3-triazol-2-yl)pyridin-2-ylamino)-6-chloropyridazine-3-carboxylate (85 mg, 246 μmol, 35%) as an off white solid. 1H NMR (400 MHz, DMSO-d) δ ppm 10.60 (s, 1H), 9.50 (s, 1H), 8.26 (s, 2H), 8.08 (t, J=8.2 Hz, 1H), 7.74 (d, J=7.8 Hz, 1H), 7.35 (d, J=8.2 Hz, 1H), 4.48 (q, J=7.3 Hz, 2H), 1.40 (t, J=7.3 Hz, 3H); MS (EI/CI) m/z: 346.0 [M+H].

Workup

temperatureThe mixture was cooled
customprecipitated by addition of acetone
filtrationThe mixture was filtered
customthe solid collected
washwas washed with methanol and ether
customthen dried

Sources & evidence

ORD record: ord-51e53488d3fd4f6689774b81f03d37b1
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901124B2

Reaction notes

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