Diisopropylethylamine → HCID 11349542, compound

HRID 600255Notes

Reaction equation

HRID 600255 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[N:14]([C:15]=2[C:16]2[CH:21]=[CH:20][N:19]=[C:18](S(C)(=O)=O)[N:17]=2)[CH:13]=[CH:12][O:11]3)=[CH:4][CH:3]=1.[NH2:26][CH2:27][C:28]([CH3:32])([CH3:31])[CH2:29][OH:30].C(N(C(C)C)CC)(C)C>CS(C)=O.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[N:14]([C:15]=2[C:16]2[CH:21]=[CH:20][N:19]=[C:18]([NH:26][CH2:27][C:28]([CH3:32])([CH3:31])[CH2:29][OH:30])[N:17]=2)[CH:13]=[CH:12][O:11]3)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 1173261-Propanol, 3-amino-2,2-dimethyl-HCID 58541669HCID 58541669, compound

Product 1

HCID 11349542HCID 11349542, compoundYield 86.1%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 6-(4-fluorophenyl)-5-[2-(methylsulfonyl)pyrimidin-4-yl]imidazo[2,1-b][1,3]oxazole (F) (0.5 g, 1.4 mmol) in dimethylsulfoxide is added 3-amino-2,2-dimethyl propanol (0.430 mg, 3.8 mmol) followed by the addition of diisopropylethylamine (0.631 g, 5.0 mmol). The mixture is heated at 100° C. overnight. After cooling to room temperature the reaction is diluted with water and extracted with dichloromethane (2×50 ml). The combined organic phase is dried over anhydrous sodium sulfate, filtered and the solvent removed in vacuo. The residue is purified by silica gel column chromatography eluting with ethyl acetate/hexane (3:1) to provide 3-({4-[6-(4-fluorophenyl)imidazo[2,1-b][1,3]oxazol-5-yl]pyrimidin-2-yl}amino)-2,2-dimethylpropan-1-ol (G) (0.46 g, 86%), m.p. 149° C.;

Workup

  1. temperatureAfter cooling to room temperature the reaction
  2. extractionextracted with dichloromethane (2×50 ml)
  3. dry with materialThe combined organic phase is dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customthe solvent removed in vacuo
  6. customThe residue is purified by silica gel column chromatography
  7. washeluting with ethyl acetate/hexane (3:1)

Sources & evidence

ORD record
ord-292c9a77b4f34982bfc420be3bae9ad2
Source dataset
uspto-grants-2011_03
Patent number
US07902192B2

Reaction notes

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