Hydrazine hydrate (1:1) → HCID 68755257, compound

HRID 1912951Notes

Reaction equation

HRID 1912951 reaction equation
O.[NH2:2][NH2:3].[CH:4]([C:6]1([CH:12]([C:15]#[N:16])[C:13]#[N:14])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)=[CH2:5]>C(O)CCC>[CH:4]([C:6]1([C:12]2[C:13]([NH2:14])=[N:2][NH:3][C:15]=2[NH2:16])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)=[CH2:5].[NH2:14][C:13]1[C:12]([C:6]2([CH2:4][CH3:5])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]2)=[C:15]([NH2:16])[NH:3][N:2]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86665182HCID 86665182, compound

Product 2

HCID 68755257HCID 68755257, compoundHCID 68756283HCID 68756283, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
100 °C

Procedure

Hydrazine monohydrate (0.098 mL, 1.69 mmol) was added to a solution of the product from Example 145B (295 mg, 1.69 mmol) in n-butanol (5 mL), and the mixture was heated at 100° C. under nitrogen for 36 hours. The reaction solution was cooled to room temperature and concentrated under vacuum. The residue was dilute with water (15 mL) and extracted with EtOAc (2×15 mL). The combined organic phase was dried (MgSO4), filtered, and concentrated under vacuum to provide the title compound as an inseparable 1:1 mixture with 3,5-diamino-4-(1-ethylcyclohexyl)pyrazole, used directly in the next step.

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. concentrationconcentrated under vacuum
  3. additionThe residue was dilute with water (15 mL)
  4. extractionextracted with EtOAc (2×15 mL)
  5. dry with materialThe combined organic phase was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-680b64161a8b45d8a04d0a93c6858405
Source dataset
uspto-grants-2013_12
Patent number
US08609669B2

Reaction notes

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