Hydrochloric Acid → HCID 86692075, compound

HRID 509266Notes

Reaction equation

HRID 509266 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1([OH:16])[CH2:8][CH2:7][CH2:6][N:5]([C:9]([O:11]C(C)(C)C)=O)[CH2:4]1.Cl.[Br:20][C:21]1[N:26]=[C:25](C(O)=O)[CH:24]=[CH:23][CH:22]=1.C(N(CC)C(C)C)(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C1COCC1.C(#N)C.CO>[Br:20][C:21]1[N:26]=[C:25]([C:9]([N:5]2[CH2:6][CH2:7][CH2:8][C:3]([OH:16])([C:2]([F:1])([F:17])[F:18])[CH2:4]2)=[O:11])[CH:24]=[CH:23][CH:22]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 5939196-Bromopyridine-2-carboxylic acidHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 50986438Tert-butyl 3-hydroxy-3-(trifluoromethyl)piperidine-1-carboxylate

Product 1

HCID 86692075HCID 86692075, compoundYield 86.1%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Procedure

After tert-butyl 3-(trifluoromethyl)-3-hydroxypiperidine-1-carboxylate (709 mg, 2.63 mmol) was dissolved in THF (10 ml), followed by addition of HCl (2.0M solution in diethyl ether, 30 ml), and then the resulting mixture was stirred at room temperature for 2 hours. The resulting reaction liquid was concentrated under reduced pressure and dried under vacuum, and then the residue thus obtained was dissolved in acetonitrile (30 ml). 6-Bromopicolinic acid (638 mg, 3.16 mmol) was added thereto, and cooled to 0° C. N,N-Diisopropylethylamine (1.1 ml, 6.58 mmol) and HBTU (1.2 g, 3.16 mmol) were sequentially added thereto, and then the resulting mixture was stirred at room temperature under nitrogen stream for 20 hours. The resulting reaction liquid was concentrated under reduced pressure, followed by addition of MC (50 ml), and then washed with distilled water. The organic layer was dried over anhydrous magnesium sulfate, followed by filtration and concentration, and then the residue thus obtained was subjected to MPLC (3% MeOH/MC), to obtain 800 mg of white solid (86%).

Workup

  1. customThe resulting reaction liquid
  2. concentrationwas concentrated under reduced pressure
  3. customdried under vacuum
  4. customthe residue thus obtained
  5. temperaturecooled to 0° C
  6. stirringthe resulting mixture was stirred at room temperature under nitrogen stream for 20 hours
  7. customThe resulting reaction liquid
  8. concentrationwas concentrated under reduced pressure
  9. additionfollowed by addition of MC (50 ml)
  10. washwashed with distilled water
  11. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  12. filtrationfollowed by filtration and concentration
  13. customthe residue thus obtained

Sources & evidence

ORD record
ord-f6a9211702b94af094727a000d0cae3f
Source dataset
uspto-grants-2015_08
Patent number
US09096571B2

Reaction notes

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