HCID 58355306, compound → HCID 58355641, compound

HRID 1260080Notes

Reaction equation

HRID 1260080 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-63c66f3e3c7e4b84bd789a5b31bc1500
Source dataset
uspto-grants-2013_06
Patent number
US08466282B2

Reaction notes

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