Tert-butyl 4-{3-[6-amino-5-chloro-2-(methyloxy)-3-pyridinyl]-3-oxopropyl}-1-piperidinecarboxylate → 1-(6-Amino-5-chloro-2-methoxy-3-pyridinyl)-3-(4-piperidinyl)-1-propanone

HRID 489793Notes

Reaction equation

HRID 489793 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[C:5]([C:10](=[O:26])[CH2:11][CH2:12][CH:13]2[CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15][CH2:14]2)=[CH:4][C:3]=1[Cl:27]>Cl>[NH2:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[C:5]([C:10](=[O:26])[CH2:11][CH2:12][CH:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)=[CH:4][C:3]=1[Cl:27]

Participants

3

Reactant 1

HCID 22262604Tert-butyl 4-{3-[6-amino-5-chloro-2-(methyloxy)-3-pyridinyl]-3-oxopropyl}-1-piperidinecarboxylate

Product 1

HCID 222625871-(6-Amino-5-chloro-2-methoxy-3-pyridinyl)-3-(4-piperidinyl)-1-propanoneYield 87%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of 1,1-dimethylethyl 4-{3-[6-amino-5-chloro-2-(methyloxy)-3-pyridinyl]-3-oxopropyl}-1-piperidinecarboxylate (step 4, 180 mg, 0.452 mmol) in 10% methanolic hydrochloric acid (2 ml) was stirred at room temperature for 18 h. After concentrated in vacuo, the mixture was dissolved in ethyl acetate (50 ml), washed with 2N aqueous sodium hydroxide (3 ml) and brine (5 ml), and dried over potassium carbonate. Removal of solvent gave 117.1 mg (87%) of the title compound as a white solid.

Workup

  1. concentrationAfter concentrated in vacuo
  2. dissolutionthe mixture was dissolved in ethyl acetate (50 ml)
  3. washwashed with 2N aqueous sodium hydroxide (3 ml) and brine (5 ml)
  4. dry with materialdried over potassium carbonate
  5. customRemoval of solvent

Sources & evidence

ORD record
ord-0546cc285e0442d887080458a432d28b
Source dataset
uspto-grants-2005_12
Patent number
US06979690B2

Reaction notes

Loading…