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

HRID 1725343Notes

Reaction equation

HRID 1725343 reaction equation
[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

Participants

7

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-d65bf6b1fa814a48a53b655c4022039c
Source dataset
uspto-grants-2009_02
Patent number
US07491714B2

Reaction notes

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