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

HRID 1396409ノート

反応式

HRID 1396409 の反応式
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

参加物

4

反応物 2

HCID 53428795Ethyl 4,6-dichloropyridazine-3-carboxylateHCID 846512026-(2H-1,2,3-triazol-2-yl)pyridin-2-amine

生成物 1

HCID 86689760ethyl 4-(6-(2H-1,2,3-triazol-2-yl)pyridin-2-ylamino)-6-chloropyridazine-3-carboxylate収率 35.4%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
140 °C

実験手順

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].

後処理

  1. temperatureThe mixture was cooled
  2. customprecipitated by addition of acetone
  3. filtrationThe mixture was filtered
  4. customthe solid collected
  5. washwas washed with methanol and ether
  6. customthen dried

出典と根拠

ORDレコード
ord-51e53488d3fd4f6689774b81f03d37b1
出典データセット
uspto-grants-2014_12
特許番号
US08901124B2

反応ノート

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