HCID 58355651, compound → HCID 58355724, compound

HRID 1184254Notes

Reaction equation

HRID 1184254 reaction equation
[F:1][CH:2]([F:45])[CH2:3][O:4][CH2:5][C:6]1[N:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:9]=[N:8][C:7]=1[C:17]([N:19]([CH2:41][CH:42]([CH3:44])[CH3:43])[C@H:20]1[CH2:25][C@@H:24]([C:26]([N:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)=[O:27])[CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21]1)=[O:18]>C(OCC)(=O)C.Cl>[F:45][CH:2]([F:1])[CH2:3][O:4][CH2:5][C:6]1[N:10]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:9]=[N:8][C:7]=1[C:17]([N:19]([CH2:41][CH:42]([CH3:43])[CH3:44])[C@H:20]1[CH2:25][C@@H:24]([C:26]([N:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)=[O:27])[CH2:23][NH:22][CH2:21]1)=[O:18]

Participants

3

Reactant 1

HCID 58355651HCID 58355651, compound

Product 1

HCID 58355724HCID 58355724, compoundYield 28.5%

Reagents, catalysts & solvents 1

HCID 21866389Hydrogen chloride-ethyl acetateSolvent

Procedure

tert-Butyl(3S,5R)-3-[({5-[(2,2-difluoroethoxy)methyl]-1-phenyl-1H-1,2,3-triazol-4-yl}carbonyl)(2-methylpropyl)amino]-5-(morpholin-4-ylcarbonyl)piperidine-1-carboxylate (15.0 mg) was dissolved in 1M hydrogen chloride-ethyl acetate (3 ml), and the mixture was stirred at room temperature for 3 hr. The reaction mixture was concentrated under reduced pressure, the residue was subjected to reversed-phase preparative HPLC and the eluted fraction was concentrated under reduced pressure. The residual aqueous layer was neutralized with 3.5M aqueous potassium carbonate solution and extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give the object product (3.6 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. concentrationthe eluted fraction was concentrated under reduced pressure
  3. extractionextracted with ethyl acetate
  4. dry with materialThe extract was dried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-0b5a18dfc2e24ec7848e6baed5502d98
Source dataset
uspto-grants-2014_03
Patent number
US08664380B2

Reaction notes

Loading…