Cesium carbonate → 2-{3-[2-(1-{[(Propan-2-ylideneamino)oxy]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}phenyl methanesulphonate

HRID 2206871Notes

Reaction equation

HRID 2206871 reaction equation
[CH3:1][C:2](=[N:4][OH:5])[CH3:3].[CH3:6][S:7]([O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH:17]1[O:21][N:20]=[C:19]([C:22]2[N:23]=[C:24]([CH:27]3[CH2:32][CH2:31][N:30]([C:33](=[O:36])[CH2:34]Cl)[CH2:29][CH2:28]3)[S:25][CH:26]=2)[CH2:18]1)(=[O:9])=[O:8].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[CH3:6][S:7]([O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH:17]1[O:21][N:20]=[C:19]([C:22]2[N:23]=[C:24]([CH:27]3[CH2:32][CH2:31][N:30]([C:33](=[O:36])[CH2:34][O:5][N:4]=[C:2]([CH3:3])[CH3:1])[CH2:29][CH2:28]3)[S:25][CH:26]=2)[CH2:18]1)(=[O:9])=[O:8]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 67180Acetone, oximeHCID 1178189342-(3-{2-[1-(Chloroacetyl)piperidin-4-yl]-1,3-thiazol-4-yl}-4,5-dihydro-1,2-oxazol-5-yl)phenyl methanesulphonate

Product 1

HCID 1178189632-{3-[2-(1-{[(Propan-2-ylideneamino)oxy]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}phenyl methanesulphonateYield 10%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of acetone oxime (9.3 mg) in N,N-dimethylformamide (0.28 ml) at room temperature was added 3 Å molecular sieve, and the mixture was stirred at this temperature for 2 hours. Thereafter, 2-(3-{2-[1-(chloroacetyl)piperidin-4-yl]-1,3-thiazol-4-yl}-4,5-dihydro-1,2-oxazol-5-yl)phenyl methanesulphonate (50 mg) and caesium carbonate (64 mg) were added thereto, and the mixture was stirred at room temperature for 18 hours. Subsequently, the mixture was filtered and extracted twice with ethyl acetate. The combined organic phases were dried over magnesium sulphate and concentrated. Purification by column chromatography gave 2-{3-[2-(1-{[(propan-2-ylideneamino)oxy]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}phenyl methanesulphonate (5 mg, 10%).

Workup

  1. stirringthe mixture was stirred at room temperature for 18 hours
  2. filtrationSubsequently, the mixture was filtered
  3. extractionextracted twice with ethyl acetate
  4. dry with materialThe combined organic phases were dried over magnesium sulphate
  5. concentrationconcentrated
  6. customPurification by column chromatography

Sources & evidence

ORD record
ord-fa968e62d1ac4300bb1d37d2ea9db49b
Source dataset
uspto-grants-2016_06
Patent number
US09375009B2

Reaction notes

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