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

HRID 1431108ノート

反応式

HRID 1431108 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 284Formic Acid溶媒HCID 712Formaldehyde溶媒

反応条件

温度
70 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-96af914b4d0d480aae39848598adb8aa
出典データセット
uspto-grants-2015_01
特許番号
US08940741B2

反応ノート

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