3-Hydroxypiperidine → HCID 89689614, compound

HRID 877544Notes

Reaction equation

HRID 877544 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[S:9][CH:10]=[C:11]([C:13]([OH:15])=O)[N:12]=2)=[C:4]([NH:16][CH:17]([CH3:19])[CH3:18])[CH:3]=1.[NH:20]1[CH2:25][CH2:24][CH2:23][CH:22]([OH:26])[CH2:21]1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[S:9][CH:10]=[C:11]([C:13]([N:20]3[CH2:25][CH2:24][CH2:23][CH:22]([OH:26])[CH2:21]3)=[O:15])[N:12]=2)=[C:4]([NH:16][CH:17]([CH3:19])[CH3:18])[CH:3]=1

Participants

6

Reactant 4

HCID 232933-HydroxypiperidineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 89689766HCID 89689766, compound

Product 1

HCID 89689614HCID 89689614, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The 2-(6-chloro-4-(isopropylamino)pyridin-3-yl)thiazole-4-carboxylic acid (23a) (100 mg, 0.336 mmol) was dissolved in DMF (5 mL), piperidin-3-ol (1.679 mmol) was added and stirred at room temperature. Added DIPEA (1.343 mmol), followed by addition of HATU (1.008 mmol) and stirred for 3 h. The reaction mixture was concentrated under reduced pressure to remove excess of DMF. The residue obtained was partitioned between water and EtOAc. The organic layer was separated, dried over Na2SO4, filtered and concentrated. The crude material obtained was purified by column chromatography through silica gel and MeOH: CHCl3 as eluent to afford the title compound, (2-(6-chloro-4-(isopropylamino)pyridin-3-yl)thiazol-4-yl)(3-hydroxypiperidin-1-yl)methanone.

Workup

  1. stirringstirred for 3 h
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customto remove excess of DMF
  4. customThe residue obtained
  5. customwas partitioned between water and EtOAc
  6. customThe organic layer was separated
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude material obtained
  11. customwas purified by column chromatography through silica gel and MeOH

Sources & evidence

ORD record
ord-d709d117001b4f49979df6ffcf45edb6
Source dataset
uspto-grants-2015_03
Patent number
US08987311B2

Reaction notes

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