Water → 6-chloro-2-methyl-4-(5-(1-methylpyrrolidin-3-yl)pyridin-2-ylamino)pyridazin-3(2H)-one

HRID 449616노트

반응식

HRID 449616 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[N:16]=[CH:15][C:14]([CH:17]3[CH2:21][CH2:20][N:19]([C:22](OC(C)(C)C)=O)[CH2:18]3)=[CH:13][CH:12]=2)[C:5](=[O:9])[N:6]([CH3:8])[N:7]=1.O>C(O)=O.C=O>[Cl:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[CH:12]=[CH:13][C:14]([CH:17]3[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18]3)=[CH:15][N:16]=2)[C:5](=[O:9])[N:6]([CH3:8])[N:7]=1

참가 물질

5

반응물 2

HCID 962WaterHCID 66742790Tert-butyl 3-(6-(6-chloro-2-methyl-3-oxo-2,3-dihydropyridazin-4-ylamino)pyridin-3-yl)pyrrolidine-1-carboxylate

생성물 1

HCID 667419726-chloro-2-methyl-4-(5-(1-methylpyrrolidin-3-yl)pyridin-2-ylamino)pyridazin-3(2H)-one수율 55.6%

시약·촉매·용매 2

HCID 284Formic Acid용매HCID 712Formaldehyde용매

반응 조건

온도
70 °C

실험 절차

Tert-butyl 3-(6-(6-chloro-2-methyl-3-oxo-2,3-dihydropyridazin-4-ylamino)pyridin-3-yl)pyrrolidine-1-carboxylate (160 mg, 394 μmol, Eq: 1.00) was dissolved in a solvent mixture of formic acid (6.0 ml) and formaldehyde, 37% (12.0 ml). The solution stirred at 70° C. for 18 h. The solution was cooled to room temperature. Water was added. The reaction mixture was extracted once with DCM. Solid K2CO3 was slowly added to the aqueous layer until the pH=14. A solid formed that was subsequently filtered. The solid was dried to give 6-chloro-2-methyl-4-(5-(1-methylpyrrolidin-3-yl)pyridin-2-ylamino)pyridazin-3(2H)-one (70 mg, 55%). LC/MS-ESI observed [M+H]+ 320.

후처리

  1. temperatureThe solution was cooled to room temperature
  2. extractionThe reaction mixture was extracted once with DCM
  3. additionSolid K2CO3 was slowly added to the aqueous layer until the pH=14
  4. customA solid formed that
  5. filtrationwas subsequently filtered
  6. customThe solid was dried

출처 및 근거

ORD 기록
ord-9be71ec1e79d40f3bb5e79ae9bb36e16
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08481540B2

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