Hydrochloric Acid → HCID 86670974, compound

HRID 515343Notes

Reaction equation

HRID 515343 reaction equation
[F:1][C:2]([F:36])([F:35])[C:3]([C:9]1[CH:34]=[CH:33][C:12]([CH2:13][N:14]2[CH2:19][CH2:18][CH:17]([C:20]([C:23]3[CH:28]=[CH:27][C:26]([NH:29]C(=O)C)=[CH:25][CH:24]=3)([OH:22])[CH3:21])[CH2:16][CH2:15]2)=[CH:11][CH:10]=1)([OH:8])[C:4]([F:7])([F:6])[F:5].Cl>C(O)C>[NH2:29][C:26]1[CH:27]=[CH:28][C:23]([C:20]([CH:17]2[CH2:16][CH2:15][N:14]([CH2:13][C:12]3[CH:33]=[CH:34][C:9]([C:3]([OH:8])([C:4]([F:7])([F:5])[F:6])[C:2]([F:1])([F:35])[F:36])=[CH:10][CH:11]=3)[CH2:19][CH2:18]2)([OH:22])[CH3:21])=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86670973HCID 86670973, compound

Product 1

HCID 86670974HCID 86670974, compoundYield 52.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

N-(4-(1-(1-(4-(1,1,1,3,3,3-Hexafluoro-2-hydroxypropan-2-yl)benzyl)piperidin-4-yl)-1-hydroxyethyl)phenyl)acetamide (0.482 mmol, 250 mg) was dissolved in ethanol (5 mL) and 2M hydrochloric acid (12.00 mmol, 6 mL) added. The mixture was heated to 100° C. for 5 hours then cooled. The mixture was purified by strong cation exchange column chromatography and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluting with dichloromethane to 10% methanol/dichloromethane) to afford the title compound (120 mg). MS (ESI) m/z 477.2 [M+H]+

Workup

  1. temperaturethen cooled
  2. customThe mixture was purified by strong cation exchange column chromatography
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (eluting with dichloromethane to 10% methanol/dichloromethane)

Sources & evidence

ORD record
ord-6bc9c09ce99147eb92d045aa3599e441
Source dataset
uspto-grants-2015_08
Patent number
US09108939B2

Reaction notes

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