Hydrazine hydrate (1:1) → HCID 68683563, compound

HRID 1713905Notes

Reaction equation

HRID 1713905 reaction equation
CO[C:3](=[O:23])[C:4]([NH:6][C:7]1[CH:8]=[CH:9][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.[NH2:25][NH2:26]>C(O)C>[NH:25]([C:3](=[O:23])[C:4]([NH:6][C:7]1[CH:8]=[CH:9][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])[NH2:26]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 68685712HCID 68685712, compound

Product 1

HCID 68683563HCID 68683563, compoundYield 80.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a vigorously stirred suspension of methyl 1-(5-{[methoxy(oxo)acetyl]amino}pyridin-2-yl)piperidine-4-carboxylate (3.12 g, 9.71 mmol) in absolute ethanol was added hydrazine monohydrate (0.52 mL, 10.76 mmol) and the suspension was allowed to stir at ambient temperature for 2 hours. The suspension was filtered, washed with ether (4×100 mL) and dried under vacuum at ambient temperature to provide the title compound (2.62 g, 7.81 mmol, 80%). 1H NMR δ 1.18 (s, 3H), 1.40-1.47 (m, 2H), 1.98-2.03 (m, 2H), 3.07-3.14 (m, 3H), 3.66 (s, 3H), 3.80-3.86 (m, 2H), 4.58 (s, 1H), 6.83 (d, 1H), 7.90 (d, 1H), 8.49 (s, 1H), 10.17 (s, 1H), 10.46 (s, 1H); MS m/e MH+ 336.

Workup

  1. filtrationThe suspension was filtered
  2. washwashed with ether (4×100 mL)
  3. customdried under vacuum at ambient temperature

Sources & evidence

ORD record
ord-0c4467b4f32b47f3b606cd91c1244e57
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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