HCID 58355651, compound → HCID 58355724, compound

HRID 1509589Notes

Reaction equation

HRID 1509589 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-50c8e4a7e3da4308863d463d45981ba8
Source dataset
uspto-grants-2015_12
Patent number
US09221836B2

Reaction notes

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