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

HRID 1396409노트

반응식

HRID 1396409 반응식
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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
140 °C

실험 절차

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].

후처리

  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

출처 및 근거

ORD 기록
ord-51e53488d3fd4f6689774b81f03d37b1
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901124B2

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