Sodium cyanoborohydride → (S)-6-Chloro-4-(5-(2-methyl-4-(oxetan-3-yl)piperazin-1-yl)pyridin-2-ylamino)pyridazin-3(2H)-one

HRID 1022074ノート

反応式

HRID 1022074 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([N:16]3[CH2:21][CH2:20][NH:19][CH2:18][C@@H:17]3[CH3:22])=[CH:12][N:11]=2)[C:5](=[O:8])[NH:6][N:7]=1.[O:23]1[CH2:26][C:25](=O)[CH2:24]1.[BH3-]C#N.[Na+]>[Cl-].[Cl-].[Zn+2].CO>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([N:16]3[CH2:21][CH2:20][N:19]([CH:25]4[CH2:26][O:23][CH2:24]4)[CH2:18][C@@H:17]3[CH3:22])=[CH:12][N:11]=2)[C:5](=[O:8])[NH:6][N:7]=1

参加物

6

反応物 3

HCID 5003444Sodium cyanoborohydrideHCID 150242543-OxetanoneHCID 86684485(S)-6-Chloro-4-(5-(2-methylpiperazin-1-yl)pyridin-2-ylamino)pyridazin-3(2H)-one

生成物 1

HCID 86684486(S)-6-Chloro-4-(5-(2-methyl-4-(oxetan-3-yl)piperazin-1-yl)pyridin-2-ylamino)pyridazin-3(2H)-one収率 56%

試薬・触媒・溶媒 2

HCID 3007855Zincchloride触媒HCID 887Methanol溶媒

実験手順

A 50-mL round-bottomed flask equipped with a magnetic stirrer was charged with 253c (321 mg, 1.0 mmol), 3-oxetanone (142 mg, 2.0 mmol), NaBH3CN (125 mg, 2.0 mmol), ZnCl2 (272 mg, 2.0 mmol), and methanol (10 mL). The mixture was stirred at room temperature overnight and concentrated under reduced pressure. Water (20 mL) was added to the residue and the resulting mixture was extracted with dichloromethane (3×20 mL). The combined organic layer was concentrated under reduced pressure and the residue was purified by silica-gel column chromatography eluting with ethyl acetate to afford 253d (210 mg, 56%) as yellow solid. MS-ESI: [M+H]+ 377.3.

後処理

  1. customA 50-mL round-bottomed flask equipped with a magnetic stirrer
  2. concentrationconcentrated under reduced pressure
  3. additionWater (20 mL) was added to the residue
  4. extractionthe resulting mixture was extracted with dichloromethane (3×20 mL)
  5. concentrationThe combined organic layer was concentrated under reduced pressure
  6. customthe residue was purified by silica-gel column chromatography
  7. washeluting with ethyl acetate

出典と根拠

ORDレコード
ord-38182c8b90b040f59d1b9a8d9335e12b
出典データセット
uspto-grants-2014_05
特許番号
US08716274B2

反応ノート

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