Sodium Hydroxide → 5-Amino-2-(2-furyl)-7-(4-(5-methylisoxazol-3-ylmethyl)piperazinyl)[1,2,4]triazolo[1,5-c]pyrimidine

HRID 1264876노트

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HRID 1264876 반응식
[NH2:1][C:2]1[N:7]2[N:8]=[C:9]([C:11]3[O:12][CH:13]=[CH:14][CH:15]=3)[N:10]=[C:6]2[CH:5]=[C:4]([N:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)[N:3]=1.[CH3:22][C:23]1[O:27][N:26]=[C:25]([CH:28]=O)[CH:24]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>O.C(O)(=O)C.ClCCl>[NH2:1][C:2]1[N:7]2[N:8]=[C:9]([C:11]3[O:12][CH:13]=[CH:14][CH:15]=3)[N:10]=[C:6]2[CH:5]=[C:4]([N:16]2[CH2:17][CH2:18][N:19]([CH2:28][C:25]3[CH:24]=[C:23]([CH3:22])[O:27][N:26]=3)[CH2:20][CH2:21]2)[N:3]=1

참가 물질

8

반응물 4

HCID 14798Sodium HydroxideHCID 27952225-Methyl-1,2-oxazole-3-carbaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 186136985-Amino-2-(2-furyl)-7-piperazinyl[1,2,4]triazolo[1,5-c]pyrimidine

생성물 1

HCID 186136925-Amino-2-(2-furyl)-7-(4-(5-methylisoxazol-3-ylmethyl)piperazinyl)[1,2,4]triazolo[1,5-c]pyrimidine수율 11.1%

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 962Water용매HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

Into 15 mL of dichloromethane, 1.50 g (5.26 mmol) of Compound F and 934 mg (8.42 mmol) of 5-methylisoxazole-3-carboxaldehyde were dissolved, and the solution was cooled to 0° C. in an ice bath. Then, 1.5 mL of acetic acid and 1.78 g (8.42 mmol; 1.6 eq.) of sodium triacetoxyborohydride were added thereto, followed by stirring at room temperature overnight. After completion of the reaction, water was added to the reaction mixture, and a 1.0 mol/L aqueous sodium hydroxide solution was further added thereto to adjust the solution to be basic. Then, the mixture was extracted by adding chloroform, and the organic layer was washed with water and brine, and then dried over anhydrous magnesium sulfate. After evaporation of the solvent, the resulting residue was purified by silica gel column chromatography (2% methanol-chloroform) and then recrystallized from ethanol to obtain 222 mg of Compound 21 as white powder (yield: 11%).

후처리

  1. additionwas added to the reaction mixture
  2. extractionThen, the mixture was extracted
  3. additionby adding chloroform
  4. washthe organic layer was washed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customAfter evaporation of the solvent
  7. customthe resulting residue was purified by silica gel column chromatography (2% methanol-chloroform)
  8. customrecrystallized from ethanol

출처 및 근거

ORD 기록
ord-8a4ace6c8dd44c57a3f5ca4b8fffc4db
출처 데이터셋
uspto-grants-2003_04
특허 번호
US06545000B1

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