Sodium Bicarbonate → (S)-4-chloro-1-(1-methoxymethyl-3-methoxypropyl)-6-methyl-1H-1,2,3-triazolo[4,5-c]pyridine

HRID 1066750ノート

反応式

HRID 1066750 の反応式
[NH2:1][C:2]1[C:3]([Cl:18])=[N:4][C:5]([CH3:17])=[CH:6][C:7]=1[NH:8][CH:9]([CH2:14][O:15][CH3:16])[CH2:10][CH2:11][O:12][CH3:13].[N:19]([O-])=O.[Na+].C([O-])(O)=O.[Na+]>C(Cl)Cl.C(O)(=O)C.O>[Cl:18][C:3]1[C:2]2[N:1]=[N:19][N:8]([C@H:9]([CH2:14][O:15][CH3:16])[CH2:10][CH2:11][O:12][CH3:13])[C:7]=2[CH:6]=[C:5]([CH3:17])[N:4]=1

参加物

7

反応物 3

HCID 516892Sodium BicarbonateHCID 23668193Sodium NitriteHCID 540346673-amino-2-chloro-6-methyl-4-N-(1-methoxymethyl-3-methoxypropyl)pyridin-4-amine

生成物 1

HCID 53925349(S)-4-chloro-1-(1-methoxymethyl-3-methoxypropyl)-6-methyl-1H-1,2,3-triazolo[4,5-c]pyridine

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒2 回HCID 962Water溶媒2 回HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

3-amino-2-chloro-6-methyl-4-N-(1-methoxymethyl-3-methoxypropyl)pyridin-4-amine (4.1 g, 14.98 mmol) was dissolved in a mixture of CH2Cl2 (40 mL) and 50% acetic acid (40 mL) and cooled to 0 ° C. in an ice bath. To that a solution of NaNO2 (1.84 g, 26.86 mmol) in water (10 mL) was added dropwise and the reaction was stirred at 0° C. for 30 min and at 25° C. for 1.5 h. Then the acetic acid was neutralized with solid NaHCO3 and water (80 mL) was added. The mixture was extracted with EtOAc (2×100 mL) and the combined organic extracts were combined and washed with brine (50 mL), dried and stripped in vacuo. The residue was chromatographed on silica gel (40% EtOAc/hexanes eluent) to give the product (4.05 g, 56% overall for the eight steps).

後処理

  1. additionwas added
  2. extractionThe mixture was extracted with EtOAc (2×100 mL)
  3. washwashed with brine (50 mL)
  4. customdried
  5. customThe residue was chromatographed on silica gel (40% EtOAc/hexanes eluent)
  6. customto give the product (4.05 g, 56% overall for the eight steps)

出典と根拠

ORDレコード
ord-d57f6163660d4a9d9855c64281b4e246
出典データセット
uspto-grants-2001_06
特許番号
US06245769B1

反応ノート

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