Ammonia → 6-Chloro-4-(5,6-dimethylpyridin-2-ylamino)pyridazine-3-carboxamide

HRID 1396350노트

반응식

HRID 1396350 반응식
[Cl:1][C:2]1[N:7]=[N:6][C:5]([C:8](OCC)=[O:9])=[C:4]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[C:16]([CH3:21])[N:15]=2)[CH:3]=1.[NH3:22].CO>>[Cl:1][C:2]1[N:7]=[N:6][C:5]([C:8]([NH2:22])=[O:9])=[C:4]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[C:16]([CH3:21])[N:15]=2)[CH:3]=1

참가 물질

4

반응물 3

HCID 222AmmoniaHCID 887MethanolHCID 86689719Ethyl 6-chloro-4-(5,6-dimethylpyridin-2-ylamino)pyridazine-3-carboxylate

생성물 1

HCID 866897206-Chloro-4-(5,6-dimethylpyridin-2-ylamino)pyridazine-3-carboxamide수율 100%

반응 조건

온도
50 °C

실험 절차

A pressure tube was charged with ethyl 6-chloro-4-(5,6-dimethylpyridin-2-ylamino)pyridazine-3-carboxylate (133 mg, 434 μmol) and 7N ammonia in methanol (9.44 g, 12 mL, 84.0 mmol). The mixture was heated in an oil bath at 50° C. for 18 h. After cooling to room temperature the reaction mixture was concentrated in vacuo to afford 6-chloro-4-(5,6-dimethylpyridin-2-ylamino)pyridazine-3-carboxamide (160 mg, 100%) as a yellow solid. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 11.48 (br. s., 1H) 9.18 (s, 1H) 8.17 (br. s., 1H) 7.43 (d, J=8.34 Hz, 1H) 6.74 (d, J=7.83 Hz, 1H) 5.67 (br. s., 1H) 2.53 (s, 3H) 2.28 (s, 3H); LCMS (EI/CI) m/z: 278 [M+H]. This material was used directly in the next step without further purification.

후처리

  1. temperatureAfter cooling to room temperature the reaction mixture
  2. concentrationwas concentrated in vacuo

출처 및 근거

ORD 기록
ord-afc1b2a68e4c4411bb4921031bfb41b6
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901124B2

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