1,4-Dioxane → HCID 178505899, compound

HRID 406293Notes

Reaction equation

HRID 406293 reaction equation
CC([CH:5]([N:15]([C@H:19]1[CH2:22][C@H:21]([O:23][C:24]2[CH:29]=[CH:28][C:27]([F:30])=[C:26]([C:31]([F:34])([F:33])[F:32])[CH:25]=2)[CH2:20]1)C(=O)[O-])[C:6]1[C:7]2[N:8]([CH:12]=[CH:13][N:14]=2)[CH:9]=[CH:10][CH:11]=1)(C)C.O1CCOCC1>Cl.CS(C)=O.CO>[F:30][C:27]1[CH:28]=[CH:29][C:24]([O:23][C@H:21]2[CH2:22][C@H:19]([NH:15][CH2:5][C:6]3[C:7]4[N:8]([CH:12]=[CH:13][N:14]=4)[CH:9]=[CH:10][CH:11]=3)[CH2:20]2)=[CH:25][C:26]=1[C:31]([F:33])([F:32])[F:34]

Participants

5

Reactant 2

HCID 312751,4-DioxaneHCID 178442166HCID 178442166, compound

Product 1

HCID 178505899HCID 178505899, compoundYield 34.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 22036561Dimethyl sulfoxide methanolSolvent

Procedure

1,1-Dimethylethyl(trans-3-{[4-fluoro-3-(trifluoromethyl)phenyl]oxy}cyclobutyl)(imidazo[1,2-a]pyridin-8-ylmethyl)carbamate (62 mg, 0.129 mmol) was stirred in 4M HCl in dioxane (5 mL, 20 mmol) for 3 hours when LCMS indicated the reaction to be complete. The mixture was loaded onto a SCX cartridge (2 g) and eluted with MeOH (3 column volumes) and flushed with ammonia in MeOH. The eluant was concentrated in vacuo to give slightly impure product which was dissolved in 50:50 DMSO/MeOH (1 mL) and purified by MDAP to give the title compound (16.8 mg).

Workup

  1. customthe reaction
  2. washeluted with MeOH (3 column volumes)
  3. customflushed with ammonia in MeOH
  4. concentrationThe eluant was concentrated in vacuo
  5. customto give slightly impure product which
  6. custompurified by MDAP

Sources & evidence

ORD record
ord-455da437546f477495530a823f32feb9
Source dataset
uspto-grants-2014_06
Patent number
US08754101B2

Reaction notes

Loading…