Hydrazine hydrate (1:1) → HCID 178500683, compound

HRID 1713826Notes

Reaction equation

HRID 1713826 reaction equation
[CH3:1][O:2][C:3](=[O:24])[CH2:4][CH:5]1[CH2:10][CH2:9][CH:8]([C:11]2[N:16]=[CH:15][C:14]([NH:17][C:18](=[O:23])[C:19](OC)=[O:20])=[CH:13][CH:12]=2)[CH2:7][CH2:6]1.O.[NH2:26][NH2:27]>C(O)C>[NH:26]([C:19](=[O:20])[C:18]([NH:17][C:14]1[CH:13]=[CH:12][C:11]([C@H:8]2[CH2:9][CH2:10][C@H:5]([CH2:4][C:3]([O:2][CH3:1])=[O:24])[CH2:6][CH2:7]2)=[N:16][CH:15]=1)=[O:23])[NH2:27]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 59464246HCID 59464246, compound

Product 1

HCID 178500683HCID 178500683, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of methyl ({6-[4-(2-methoxy-2-oxoethyl)cyclohexyl]pyridin-3-yl}amino)(oxo)acetate, prepared as above, (865 mg, 2.59 mmol) in absolute ethanol (50 mL) was added hydrazine monohydrate (0.15 mL, 3.09 mmol). A thick white suspension formed which was then allowed to stir at ambient temperature for ˜1.5 hrs, filtered, washed with ether (2×20 mL) and then dried to give the title compound (Intermediate 78), 610 mg (1.82 mmol, 70%) as a solid; 1H NMR δ 1.09-1.21 (m, 2H), 1.47-1.56 (m, 2H), 1.71-1.87 (m, 5H), 2.25 (d, 2H), 2.54-2.63 (m, 1H), 3.60 (s, 3H), 4.62 (s, 2H), 7.24 (d, 1H), 8.07 (d, 1H), 8.85 (s, 1H), 10.27 (s, 1H) (not all NH protons seen); MS m/e MH+ 335.

Workup

  1. customA thick white suspension formed which
  2. filtrationfiltered
  3. washwashed with ether (2×20 mL)
  4. customdried

Sources & evidence

ORD record
ord-2d8092991447456296055213f2e6f224
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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