Hydrazine hydrate (1:1) → HCID 86680430, compound

HRID 1023190Notes

Reaction equation

HRID 1023190 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[N:7]1[C:15]2[C:10](=[CH:11][C:12]([CH2:16][CH2:17][C:18]([O:20]CC)=O)=[CH:13][CH:14]=2)[CH:9]=[N:8]1.O.[NH2:24][NH2:25]>C(O)C>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[N:7]1[C:15]2[C:10](=[CH:11][C:12]([CH2:16][CH2:17][C:18]([NH:24][NH2:25])=[O:20])=[CH:13][CH:14]=2)[CH:9]=[N:8]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86680429HCID 86680429, compound

Product 1

HCID 86680430HCID 86680430, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of ethyl 3-(1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-yl)propanoate (0.59 g, 1.951 mmol) in ethanol (5 mL) was added hydrazine hydrate (0.306 mL, 9.76 mmol) and the reaction was heated at 80° C. overnight. The solid which formed was filtered and dried to afford 3-(1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-yl) propanehydrazide (0.56 g, 82%), used without further purification. 1HNMR: 400 MHz, DMSO-d6: δ 1.58-1.59 (m, 2H), 1.92-1.96 (m, 1H), 1.97-2021.00 (m, 1H), 2.34-2.42 (m, 3H), 2.90-2.92 (m, 2H), 3.72-3.76 (m, 1H), 3.86-3.89 (m, 1H), 4.14 (s, 4H), 5.79-5.79 (m, 1H), 7.25-7.26 (m, 1H), 7.54 (s, 1H), 7.62 (d, J=8.80 Hz, 1H), 8.01 (s, 1H), 8.94 (s, 2H). LCMS: RT 0.64 min; LCMS (ES-API), m/z 205 (M-THP).

Workup

  1. customThe solid which formed
  2. filtrationwas filtered
  3. customdried

Sources & evidence

ORD record
ord-65f3dffed9594ce69f0e72222512f0e3
Source dataset
uspto-grants-2014_05
Patent number
US08722670B2

Reaction notes

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