HCID 86717982, compound → HCID 86717981, compound

HRID 2275893Notes

Reaction equation

HRID 2275893 reaction equation
FC(F)(F)C(O)=O.[F:8][C:9]1[CH:44]=[CH:43][CH:42]=[C:41]([F:45])[C:10]=1[CH2:11][O:12][C:13]1[C:14]2[N:15]([C:20]([C:24]([NH:26][CH2:27][C@H:28]3[CH2:33][CH2:32][CH2:31][CH2:30][N:29]3C(OC(C)(C)C)=O)=[O:25])=[C:21]([CH3:23])[N:22]=2)[CH:16]=[C:17]([CH3:19])[CH:18]=1>Cl.C(OCC)C>[F:45][C:41]1[CH:42]=[CH:43][CH:44]=[C:9]([F:8])[C:10]=1[CH2:11][O:12][C:13]1[C:14]2[N:15]([C:20]([C:24]([NH:26][CH2:27][C@H:28]3[CH2:33][CH2:32][CH2:31][CH2:30][NH:29]3)=[O:25])=[C:21]([CH3:23])[N:22]=2)[CH:16]=[C:17]([CH3:19])[CH:18]=1

Participants

4

Reactant 1

HCID 86717982HCID 86717982, compound

Product 1

HCID 86717981HCID 86717981, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 3283Diethyl EtherSolvent

Procedure

56 mg of tert-butyl (2R)-2-{[({8-[(2,6-difluorobenzyl)oxy]-2,6-dimethylimidazo[1,2-a]pyridin-3-yl}carbonyl)amino]methyl}piperidin-1-carboxylate trifluoroacetate Example 183A (0.09 mmol) were initially charged in 2 M hydrochloric acid in diethyl ether, and the mixture was stirred at RT for 5 h. The resulting precipitate was filtered off and washed with diethyl ether, dissolved in dichloromethane and washed with saturated aqueous sodium bicarbonate solution. The aqueous phase was extracted twice with dichloromethane and the combined organic phases were dried over sodium sulphate, filtered, concentrated and lyophilized. This gave 30 mg (78% of theory; purity 95%) of the title compound.

Workup

  1. filtrationThe resulting precipitate was filtered off
  2. washwashed with diethyl ether
  3. dissolutiondissolved in dichloromethane
  4. washwashed with saturated aqueous sodium bicarbonate solution
  5. extractionThe aqueous phase was extracted twice with dichloromethane
  6. dry with materialthe combined organic phases were dried over sodium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-602e5ebd02af4e909c081c914be39a77
Source dataset
uspto-grants-2015_09
Patent number
US09126998B2

Reaction notes

Loading…