p-Toluenesulfonic acid → HCID 117940031, compound

HRID 2199840Notes

Reaction equation

HRID 2199840 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH:8]([CH2:13][C:14]3[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=3)[C:9]2=[O:12])=[CH:5][C:4]=1[N:20]1[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]1.CC1C=CC(S(O)(=O)=O)=CC=1.[F:38][C:39]([F:47])([F:46])[C:40]([C:42]([F:45])([F:44])[F:43])=[O:41]>C1(C)C=CC=CC=1.O>[F:38][C:39]([F:47])([F:46])[C:40]([C:18]1[CH:19]=[C:14]([CH2:13][CH:8]2[CH2:7][C:6]3[C:10](=[CH:11][C:3]([O:2][CH3:1])=[C:4]([N:20]4[CH2:21][CH2:22][N:23]([CH3:26])[CH2:24][CH2:25]4)[CH:5]=3)[C:9]2=[O:12])[CH:15]=[N:16][CH:17]=1)([OH:41])[C:42]([F:45])([F:44])[F:43]

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 12695HexafluoroacetoneHCID 117940146HCID 117940146, compound

Product 1

HCID 117940031HCID 117940031, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

To a stirred solution of 255 (0.05 g, 0.142 mmol) in toluene was added PTSA (0.054 g, 0.284 mmol) and kept stirring at 120° C. Hexafluoroacetone 244 (0.078 g, 0.356 mmol) was added to the reaction and kept at temperature and stirred for 16 h. Reaction was then cooled to RT, diluted with water, and extracted with ethyl acetate twice, The organic layer was dried over sodium sulphate and concentrated to get the crude, which was purified through flash chromatography by using 100-200 mesh silica gel and eluting the compound at 30% ethyl acetate in hexane as thick sticky solid 2-((5-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)pyridin-3-yl)methyl)-6-methoxy-5-(4-methylpiperazin-1-yl)-2,3-dihydro-1H-inden-1-one 256.

Workup

  1. stirringstirred for 16 h
  2. customReaction
  3. temperaturewas then cooled to RT
  4. extractionextracted with ethyl acetate twice
  5. dry with materialThe organic layer was dried over sodium sulphate
  6. concentrationconcentrated
  7. customto get the crude, which
  8. customwas purified through flash chromatography
  9. washeluting the compound at 30% ethyl acetate in hexane as thick sticky solid 2-((5-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)pyridin-3-yl)methyl)-6-methoxy-5-(4-methylpiperazin-1-yl)-2,3-dihydro-1H-inden-1-one 256

Sources & evidence

ORD record
ord-7b549695dff44d4d8f406a1f3198b86a
Source dataset
uspto-grants-2016_06
Patent number
US09359315B2

Reaction notes

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