Hydrazine → HCID 178456808, compound

HRID 1452985Notes

Reaction equation

HRID 1452985 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=O)[CH:9]([C:12]1[N:17]=[C:16]2[S:18][C:19]([NH:21][CH:22]([CH3:24])[CH3:23])=[N:20][C:15]2=[CH:14][CH:13]=1)[C:10]#[N:11].[NH2:26][NH2:27]>CCO.CC(O)=O>[NH2:11][C:10]1[NH:27][N:26]=[C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:2]=2)[C:9]=1[C:12]1[N:17]=[C:16]2[S:18][C:19]([NH:21][CH:22]([CH3:24])[CH3:23])=[N:20][C:15]2=[CH:14][CH:13]=1

Participants

5

Reactant 2

HCID 9321HydrazineHCID 57527174HCID 57527174, compound

Product 1

HCID 178456808HCID 178456808, compoundYield 1.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

To a solution of 3-(2-fluorophenyl)-2-(2-(isopropylamino)thiazolo[5,4-b]pyridin-5-yl)-3-oxopropanenitrile (0.10 g, 0.282 mmol, 1.0 eq.) in EtOH (1 mL) and HOAc (2 mL) at 0° C. was added hydrazine (0.1 mL, 3.19 mmol, 11.3 eq.). After 10 min., the cold bath was removed, and the reaction mixture was stirred to room temperature for 10 min. It was then heated at 88° C. for 5 hr and at 100° C. overnight. After cooling to room temperature and then to 0° C., water was added followed by concentrated aqueous NH4OH until pH was 10 by litmus paper. The aqueous layer was extracted with EtOAc (3×). The organic layers were combined, dried over Na2SO4, filtered, and concentrated in vacuo. MeOH was added to the residue, and the mixture was subjected to autoprep. The appropriate fractions were collected, and NaHCO3 (s) was added. The solution was then concentrated in vacuo not to dryness and extracted with CH2Cl2 (3×). The organic layers were combined, dried over Na2SO4, filtered, and concentrated in vacuo to give 5-(5-amino-3-phenyl-1H-pyrazol-4-yl) -N-isopropylthiazolo[5,4-b]pyridin-2-amine as a light yellow solid (0.0014 g, 1.3% yield). LC/MS (MH)=369.14.

Workup

  1. customthe cold bath was removed
  2. temperatureIt was then heated at 88° C. for 5 hr and at 100° C. overnight
  3. temperatureAfter cooling to room temperature
  4. additionto 0° C., water was added
  5. extractionThe aqueous layer was extracted with EtOAc (3×)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. additionMeOH was added to the residue
  10. customThe appropriate fractions were collected
  11. additionNaHCO3 (s) was added
  12. concentrationThe solution was then concentrated in vacuo not to dryness
  13. extractionextracted with CH2Cl2 (3×)
  14. dry with materialdried over Na2SO4
  15. filtrationfiltered
  16. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-21c8d80cd49947249b4ede9b7ec4ac72
Source dataset
uspto-grants-2009_01
Patent number
US07473784B2

Reaction notes

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