HCID 58355306, compound → HCID 58355641, compound

HRID 2169066Notes

Reaction equation

HRID 2169066 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([CH2:13][O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:11]([C:21]([N:23]([CH2:45][CH:46]([CH3:48])[CH3:47])[C@H:24]2[CH2:29][C@@H:28]([C:30]([N:32]3[CH2:37][CH2:36][O:35][CH2:34][CH2:33]3)=[O:31])[CH2:27][N:26](C(OC(C)(C)C)=O)[CH2:25]2)=[O:22])[N:10]=[N:9]1>C(OCC)(=O)C.Cl>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([CH2:13][O:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[C:11]([C:21]([N:23]([CH2:45][CH:46]([CH3:48])[CH3:47])[C@H:24]2[CH2:29][C@@H:28]([C:30]([N:32]3[CH2:37][CH2:36][O:35][CH2:34][CH2:33]3)=[O:31])[CH2:27][NH:26][CH2:25]2)=[O:22])[N:10]=[N:9]1

Participants

3

Reactant 1

HCID 58355306HCID 58355306, compound

Product 1

HCID 58355641HCID 58355641, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 21866389Hydrogen chloride-ethyl acetateSolvent

Procedure

tert-Butyl (3S,5R)-3-[{[1-(2-fluorophenyl)-5-(phenoxymethyl)-1H-1,2,3-triazol-4-yl]carbonyl}(2-methylpropyl)amino]-5-(morpholin-4-ylcarbonyl)piperidine-1-carboxylate (119 mg) was dissolved in 1M hydrogen chloride-ethyl acetate (4 ml), and the mixture was stirred at room temperature for 13 hr and concentrated under reduced pressure. The residue was diluted with ethyl acetate, washed successively with 3.5M aqueous potassium carbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was subjected to basic silica gel column chromatography, and a fraction eluted with ethyl acetate-hexane-methanol (10:90:0-100:0:0-85:0:15) was concentrated under reduced pressure. The residue was dissolved in methanol (2 ml), fumaric acid (7.9 mg) was added and the mixture was stirred at room temperature for 1 hr. The reaction mixture was concentrated under reduced pressure to give the object product (87 mg).

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionThe residue was diluted with ethyl acetate
  3. washwashed successively with 3.5M aqueous potassium carbonate solution and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. washa fraction eluted with ethyl acetate-hexane-methanol (10:90:0-100:0:0-85:0:15)
  7. concentrationwas concentrated under reduced pressure
  8. dissolutionThe residue was dissolved in methanol (2 ml)
  9. additionfumaric acid (7.9 mg) was added
  10. stirringthe mixture was stirred at room temperature for 1 hr
  11. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-d8b1354ea64d4d448ffd6bae78bbcb89
Source dataset
uspto-grants-2015_06
Patent number
US09045436B2

Reaction notes

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