p-Toluenesulfonic acid → HCID 117940099, compound

HRID 2199838Notes

Reaction equation

HRID 2199838 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][O:23][CH2:22][CH2:21]1.CC1C=CC(S(O)(=O)=O)=CC=1.[F:37][C:38]([F:46])([F:45])[C:39]([C:41]([F:44])([F:43])[F:42])=[O:40]>C1(C)C=CC=CC=1.O>[F:37][C:38]([F:46])([F:45])[C:39]([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][O:23][CH2:24][CH2:25]4)[CH:5]=3)[C:9]2=[O:12])[CH:15]=[N:16][CH:17]=1)([OH:40])[C:41]([F:44])([F:43])[F:42]

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 12695HexafluoroacetoneHCID 117940187HCID 117940187, compound

Product 1

HCID 117940099HCID 117940099, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

To a stirred solution of 243 (0.08 g, 0.236 mmol) in toluene was added PTSA (0.090 g, 0.472 mmol) and kept stirring at 120° C. Hexafluoroacetone 244 (0.129 g, 0.590 mmol) was added to the reaction and heated to 100° C. for 16 h. Reaction was cooled to RT, diluted with water, extracted with ethyl acetate twice, the organic layer dried over sodium sulphate and concentrated to get the crude, which was purified through flash chromatography by using 100-200 mesh silica gel 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-morpholino-2,3-dihydro-1H-inden-1-one 245. 1HNMR (400 MHz, CDCl3) δ ppm 7.06 (m, 2H), 6.88 (s, 1H), 6.90 (s, 1H), 6.123 (s, 1H), 3.88 (m, 7H), 3.49 (m, 1H), 3.08 (m, 2H), 3.03 (m, 6H), 2.29 (m, 2H).

Workup

  1. temperatureheated to 100° C. for 16 h
  2. customReaction
  3. temperaturewas cooled to RT
  4. extractionextracted with ethyl acetate twice
  5. dry with materialthe organic layer dried over sodium sulphate
  6. concentrationconcentrated
  7. customto get the crude, which
  8. customwas purified through flash chromatography

Sources & evidence

ORD record
ord-40c447eb4e4a4bc682dd3cdd00f4d5e8
Source dataset
uspto-grants-2016_06
Patent number
US09359315B2

Reaction notes

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