Hydrazine hydrate (1:1) → HCID 66632332, compound

HRID 409031Notes

Reaction equation

HRID 409031 reaction equation
[CH3:1][C:2]1[S:29][C:5]2=[N:6][C:7]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=3)=[C:8]([C@@H:10]([N:12]3C(=O)C4C(=CC=CC=4)C3=O)[CH3:11])[CH:9]=[C:4]2[CH:3]=1.O.NN>C(O)C.C(OCC)(=O)C>[CH3:1][C:2]1[S:29][C:5]2=[N:6][C:7]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=3)=[C:8]([C@@H:10]([NH2:12])[CH3:11])[CH:9]=[C:4]2[CH:3]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 66633726HCID 66633726, compound

Product 1

HCID 66632332HCID 66632332, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

Slurried (S)-2-(1-(2-methyl-6-(pyridin-2-yl)thieno[2,3-b]pyridin-5-yl)ethyl)isoindoline-1,3-dione (60 mg, 0.150 mmol) in 3.5 mL of ethanol was warmed to 60° C. and hydrazine monohydrate (73.0 μL, 1.502 mmol) was added. The reaction was stirred at 60° C. for 2 h, cooled to RT and diluted with ethyl acetate. The reaction was filtered and concentrated. The resulting residue was redissolved in ethyl acetate and washed with water and brine, dried over MgSO4, filtered and concentrated to afford crude (S)-1-(2-methyl-6-(pyridin-2-yl)thieno[2,3-b]pyridin-5-yl)ethanamine. 1H NMR (400 MHz, CDCl3) δ 8.67 (ddd, J=4.9, 2.7, 1.2 Hz, 1H), 8.19 (s, 1H), 7.85 (m, 2H), 7.32 (ddd J=7.0, 4.9, 1.8 Hz, 1H), 6.93 (q, J=1.2 Hz, 1H), 4.60 (q, J=6.6 Hz, 1H), 2.63 (d, J=1.2 Hz, 3H), 2.20 (br s, 3H), 1.43 (d, J=6.6 Hz, 3H) ppm. LC/MS (M+1, found=270.1).

Workup

  1. temperaturecooled to RT
  2. filtrationThe reaction was filtered
  3. concentrationconcentrated
  4. dissolutionThe resulting residue was redissolved in ethyl acetate
  5. washwashed with water and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-d55b274407784e6084339f7017347b7c
Source dataset
uspto-grants-2014_06
Patent number
US08759371B2

Reaction notes

Loading…