Hydrazine hydrate (1:1) → HCID 66632471, compound

HRID 409019Notes

Reaction equation

HRID 409019 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[N:12]=[C:11]2[S:13][CH:14]=[CH:15][C:10]2=[CH:9][C:8]=1[CH:16]([N:18]1C(=O)C2C(=CC=CC=2)C1=O)[CH3:17].O.NN>C(O)C>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[N:12]=[C:11]2[S:13][CH:14]=[CH:15][C:10]2=[CH:9][C:8]=1[CH:16]([NH2:18])[CH3:17]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 66633234HCID 66633234, compound

Product 1

HCID 66632471HCID 66632471, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

2-(1-(6-(Pyridin-2-yl)thieno[2,3-b]pyridin-5-yl)ethyl)isoindoline-1,3-dione (220 mg, 0.57 mmol) was slurried in ethanol (5 mL). To this slurry was added hydrazine hydrate (500 uL, 10.3 mmol, 18 eq). The reaction was heated to 60° C. for 2 h, then cooled to rt and filtered. The filtrate was concentrated and redissolved in ethyl acetate and water. The layers were separated and the organic layer was washed with brine, dried over MgSO4, filtered, and concentrated in vacuo to afford 1-(6-(pyridin-2-yl)thieno[2,3-b]pyridin-5-yl)-ethanamine (134 mg, 91.9% yield). 1H NMR (400 MHz, CDCl3) δ 8.69 (ddd, J=4.7, 1.6, 0.8 Hz, 1H), 8.39 (s, 1H), 7.87 (m, 2H), 7.57 (d, J=5.9 Hz, 1H), 7.34 (ddd, J=6.8, 5.1, 2.0, 1H), 7.31 (d, J=5.9 Hz, 1H), 4.63 (q, J=6.7 hz, 1H), 1.44 (d, J=6.7 Hz, 3H) ppm.

Workup

  1. temperaturecooled to rt
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated
  4. dissolutionredissolved in ethyl acetate
  5. customThe layers were separated
  6. washthe organic layer was washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bf04b469e7c04c37880fc4781526463a
Source dataset
uspto-grants-2014_06
Patent number
US08759371B2

Reaction notes

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