Ethanol → HCID 18771580, compound

HRID 479697Notes

Reaction equation

HRID 479697 reaction equation
C1(=O)[N:5]([CH2:6][CH2:7][C:8]2[N:13]=[C:12]([NH:14][C:15]([NH:17][C:18]3[N:19]=[C:20]([C:23]4[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=4)[S:21][CH:22]=3)=[O:16])[CH:11]=[CH:10][CH:9]=2)C(=O)C2=CC=CC=C12.CCO.O.NN>C(Cl)(Cl)Cl>[NH2:5][CH2:6][CH2:7][C:8]1[N:13]=[C:12]([NH:14][C:15]([NH:17][C:18]2[N:19]=[C:20]([C:23]3[CH:24]=[CH:25][N:26]=[CH:27][CH:28]=3)[S:21][CH:22]=2)=[O:16])[CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 24654Hydrazine hydrate (1:1)HCID 18771882HCID 18771882, compound

Product 1

HCID 18771580HCID 18771580, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a mixture of 1-{6-[2-(phthalimidyl)ethyl]-pyridin-2-yl}-3-(2-pyridin-4-yl-thiazol-4-yl)urea (75 mg, 0.16 mmol, Example 88) and EtOH (10 mL) was added hydrazine hydrate (0.1 mL, 0.18 mmol). The mixture was heated at reflux for 2 h then cooled to RT. The residue was dissolved in 3:1 CHCl3/IpOH, washed with saturated NaHCO3, dried (MgSO4) and concentrated in vacuo to afford the title compound as a yellow solid. MS m/z: 341.0 (M+H). Calc'd for C16H16N6OS: 340.11.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 2 h
  3. washwashed with saturated NaHCO3
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e24756ede63d48689655cd24fed6cd38
Source dataset
uspto-grants-2003_11
Patent number
US06645990B2

Reaction notes

Loading…