Hydrazine hydrate (1:1) → HCID 59464221, compound

HRID 1713912Notes

Reaction equation

HRID 1713912 reaction equation
CO[C:3](=[O:24])[C:4]([NH:6][C:7]1[CH:8]=[C:9]([CH3:23])[C:10]([N:13]2[CH2:18][CH2:17][CH:16]([C:19]([O:21][CH3:22])=[O:20])[CH2:15][CH2:14]2)=[N:11][CH:12]=1)=[O:5].O.[NH2:26][NH2:27]>CCO>[NH:26]([C:3](=[O:24])[C:4]([NH:6][C:7]1[CH:8]=[C:9]([CH3:23])[C:10]([N:13]2[CH2:14][CH2:15][CH:16]([C:19]([O:21][CH3:22])=[O:20])[CH2:17][CH2:18]2)=[N:11][CH:12]=1)=[O:5])[NH2:27]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)2×HCID 59464100HCID 59464100, compound

Product 1

HCID 59464221HCID 59464221, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methyl 1-(5-{[methoxy(oxo)acetyl]amino}-3-methylpyridin-2-yl)piperidine-4-carboxylate (2.01 g; 5.99 mmol) was dissolved in EtOH (140 mL) and treated with dropwise addition of hydrazine hydrate (320 μL; 6.59 mmol). Within a few minutes a flocculent precipitate formed. Vigorous stirring was continued for 17 hrs. A further 32 μL (0.65 mmol) hydrazine hydrate was added and stirring continued at ambient temperature for 24 hrs. The precipitated solid was filtered off, washed with ether on the filter and dried under high vacuum at 60° C. to give the title compound (1.76 g, 88% yield). This was used in the next stage without further purification. 1H NMR δ 1.59-1.80 (m, 2H), 1.83-1.98 (m, 2H), 2.16 (s, 3H), 2.52-2.60 (m, 1H), 2.66-2.84 (m, 2H), 3.22-3.37 (m, 2H), 3.58 (s, 3H), 4.54 (d, 2H), 7.89 (d, 1H), 8.47 (d, 1H), 10.14 (s, 1H), 10.48 (s, 1H). MS m/e MH+ 336.24.

Workup

  1. customWithin a few minutes a flocculent precipitate formed
  2. stirringstirring
  3. waitcontinued at ambient temperature for 24 hrs
  4. filtrationThe precipitated solid was filtered off
  5. washwashed with ether on the
  6. filtrationfilter
  7. customdried under high vacuum at 60° C.

Sources & evidence

ORD record
ord-58743e00d0974537a0d75e78df15f232
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

Loading…