Methanol → (R)-3-{3-[(benzo[1,2,5]thiadiazol-5-ylmethyl)-amino]-propyl}-5-(6-methoxyquinolin-4-yl)-oxazolidin-2-one

HRID 1725343

반응식

HRID 1725343 반응식
[NH2:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:9][C@@H:8]([C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([O:20][CH3:21])[CH:18]=3)[N:13]=[CH:12][CH:11]=2)[O:7][C:6]1=[O:22].[N:23]1[S:27][N:26]=[C:25]2[CH:28]=[C:29]([CH:32]=O)[CH:30]=[CH:31][C:24]=12.CO.[BH4-].[Na+]>C(OCC)(=O)C.C(Cl)Cl>[N:23]1[S:27][N:26]=[C:25]2[CH:28]=[C:29]([CH2:32][NH:1][CH2:2][CH2:3][CH2:4][N:5]3[CH2:9][C@@H:8]([C:10]4[C:19]5[C:14](=[CH:15][CH:16]=[C:17]([O:20][CH3:21])[CH:18]=5)[N:13]=[CH:12][CH:11]=4)[O:7][C:6]3=[O:22])[CH:30]=[CH:31][C:24]=12

참가 물질

7

반응물 4

HCID 887MethanolHCID 27762902,1,3-Benzothiadiazole-5-carbaldehydeHCID 4311764Sodium borohydrideHCID 68839629(R)-3-(3-amino-propyl)-5-(6-methoxy-quinolin-4-yl)-oxazolidin-2-one

생성물 1

HCID 10003857(R)-3-{3-[(benzo[1,2,5]thiadiazol-5-ylmethyl)-amino]-propyl}-5-(6-methoxyquinolin-4-yl)-oxazolidin-2-one수율 66.7%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of (R)-3-(3-amino-propyl)-5-(6-methoxy-quinolin-4-yl)-oxazolidin-2-one (0.15 g, 0.5 mmol), benzo[1,2,5]thiadiazole-5-carbaldehyde (92 mg, 0.56 mmol), methanol (0.5 ml), methylene chloride (1.8 ml), 3 Å dry molecular sieve (1 g) was stirred at room temperature for 16 hours. Sodium borohydride (28 mg, 0.76 mmol) was added and the mixture was stirred for 3 hours. After concentration of the solvent the residue was dissolved in ethyl acetate and the organic phase was washed with water, dried over magnesium sulfate and concentrated. The residue was chromatographed on silicagel eluting with methylene chloride-methanol (99-1 first, then 90-10) to give (R)-3-{3-[(benzo[1,2,5]thiadiazol-5-ylmethyl)-amino]-propyl}-5-(6-methoxyquinolin-4-yl)-oxazolidin-2-one (150 mg, 59%).

후처리

  1. customdry molecular sieve (1 g)
  2. stirringthe mixture was stirred for 3 hours
  3. washthe organic phase was washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silicagel
  7. washeluting with methylene chloride-methanol (99-1 first

출처 및 근거

ORD 기록
ord-d65bf6b1fa814a48a53b655c4022039c
출처 데이터셋
uspto-grants-2009_02
특허 번호
US07491714B2

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