Pyridine → HCID 59464100, compound

HRID 1713911Notes

Reaction equation

HRID 1713911 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH3:18])[C:5]([N:8]2[CH2:13][CH2:12][CH:11]([C:14]([O:16][CH3:17])=[O:15])[CH2:10][CH2:9]2)=[N:6][CH:7]=1.Cl[C:20](=[O:25])[C:21]([O:23][CH3:24])=[O:22].N1C=CC=CC=1>C(Cl)Cl>[CH3:24][O:23][C:21](=[O:22])[C:20]([NH:1][C:2]1[CH:3]=[C:4]([CH3:18])[C:5]([N:8]2[CH2:13][CH2:12][CH:11]([C:14]([O:16][CH3:17])=[O:15])[CH2:10][CH2:9]2)=[N:6][CH:7]=1)=[O:25]

Participants

5

Reactant 3

HCID 1049PyridineHCID 79846Methyl chloroglyoxylateHCID 59464112HCID 59464112, compound

Product 1

HCID 59464100HCID 59464100, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To an ice-water cooled solution of methyl 1-(5-amino-3-methylpyridin-2-yl)piperidine-4-carboxylate (2.14 g; 8.59 mmol) in DCM (43 mL) was added methyl chloro(oxo)acetate (1.03 mL; 11.17 mmol) followed by pyridine (834 μL; 10.31 mmol) and the reaction mixture was allowed to stir at ˜0° C. for 30 mins, then allowed to warm to room temperature. The reaction solution was washed with water (40 mL) then saturated brine (40 mL). The organics were dried over MgSO4, filtered and evaporated under vacuum to yield a pale tan solid (2.01 g, 70% yield). This was used for the next stage without further purification. 1H NMR δ 1.60-1.80 (m, 2H), 1.85-1.99 (m, 2H), 2.18 (s, 3H), 2.54-2.62 (m, 1H), 2.69-2.88 (m, 2H), 3.26-3.40 (m, 2H), 3.56 (s, 3H), 3.82 (s, 3H), 7.87 (d, 1H), 8.40 (d, 1H), 10.75 (s, 1H). MS m/e MH+ 336.20.

Workup

  1. temperatureto warm to room temperature
  2. washThe reaction solution was washed with water (40 mL)
  3. dry with materialThe organics were dried over MgSO4
  4. filtrationfiltered
  5. customevaporated under vacuum

Sources & evidence

ORD record
ord-33898469f47440f1a16dd1352bc02575
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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