Lithium Hydroxide → HCID 59774562, compound

HRID 967395Notes

Reaction equation

HRID 967395 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[C:20]([O:21][CH2:22][C:23]([O:25]CC)=O)=[CH:19][CH:18]=[CH:17][N:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li+].[OH-].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>O.CO>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:23](=[O:25])[CH2:22][O:21][C:20]3[CH:19]=[CH:18][CH:17]=[N:16][C:15]2=3)[CH2:10][CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59774577HCID 59774577, compound

Product 1

HCID 59774562HCID 59774562, compoundYield 48.3%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

To a stirring solution of 0.9 g (0.0023 mol) of 4-(3-ethoxycarbonylmethoxy-pyridin-2-ylamino)-piperidine-1-carboxylic acid tert-butyl ester in H2O/MeOH (1 mL/11 mL) was added 0.05 g (0.0023 mol) of LiOH. After 6 h, the solvent was removed under reduced pressure. The residue was dissolved in DMF (12 mL) and to the stirring solution was added 1.82 g (0.0048 mol) of HATU. After 3 h, the reaction was partitioned between EtOAc (250 mL) and saturated NaHCO3 (100 mL), and washed with water (3×100 mL). The combined aqueous layers were extracted with EtOAc (100 mL). The combined organic layers were washed with brine (100 mL), dried over Na2SO4, and concentrated to afford 0.37 g (46%) of a white solid. MS (electrospray): exact mass calculated for C17H23N3O4, 333.17. m/z found, 356.1 [M+Na]+. 1H NMR (400 MHz, CDCl3): 7.97 (dd, J=4.8 Hz, 1.5 Hz, 1H), 7.25 (dd, J=8.1 Hz, 1.5 Hz, 1H), 6.96 (dd, J=8.1 Hz, 4.8 Hz, 1H), 5.03 (tt, J=11.9 Hz, 4.0 Hz, 1H), 4.55 (s, 2H), 4.13 (d, J=10.9 Hz, 2H), 2.82-2.69 (m, 2H), 2.68 (qd, J=12.4 Hz, 4.0 Hz, 2H), 1.65 (d, J=12.1 Hz, 2H), 1.46 (s, 9H).

Workup

  1. customthe solvent was removed under reduced pressure
  2. dissolutionThe residue was dissolved in DMF (12 mL) and to the stirring solution
  3. waitAfter 3 h
  4. customthe reaction was partitioned between EtOAc (250 mL) and saturated NaHCO3 (100 mL)
  5. washwashed with water (3×100 mL)
  6. extractionThe combined aqueous layers were extracted with EtOAc (100 mL)
  7. washThe combined organic layers were washed with brine (100 mL)
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-1bf6aafe0b0a4a898870e58eb86ba45a
Source dataset
uspto-grants-2005_10
Patent number
US06953793B2

Reaction notes

Loading…