HCID 18771677, compound → HCID 10270448, compound

HRID 460254Notes

Reaction equation

HRID 460254 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[S:9][CH:10]=[C:11]([NH:13][C:14]([NH:16][C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([CH2:23][CH3:24])[N:18]=3)=[O:15])[N:12]=2)[CH:5]=[CH:4][N:3]=1.[CH3:25][CH2:26][O-:27].[Na+].CCO>O>[CH2:26]([O:27][C:2]1[CH:7]=[C:6]([C:8]2[S:9][CH:10]=[C:11]([NH:13][C:14]([NH:16][C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([CH2:23][CH3:24])[N:18]=3)=[O:15])[N:12]=2)[CH:5]=[CH:4][N:3]=1)[CH3:25]

Participants

4

Reactant 2

HCID 18771677HCID 18771677, compoundHCID 23706232Ethanol sodium ethoxide

Product 1

HCID 10270448HCID 10270448, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 10 mL round bottom flask containing 1-[2-(2-chloropyridin-4-yl)thiazol-4-yl]-3-(6-ethylpyridin-2-yl)urea (40 mg, 0.11 mmol) (prepared similar to that described for Example 95) was charged a 21 wt % NaOEt/EtOH solution (5 mL). The reaction mixture was heated to reflux. After 2 h, the reaction mixture was cooled to RT and diluted with H2O then concentrated in vacuo. The solid residue was washed with CH2Cl2 and EtOAc then the solid was diluted with MeOH and concentrated in vacuo. The residue was diluted with EtOAc; washed with saturated NH4Cl and H2O, dried (MgSO4) and concentrated in vacuo to afford the title compound as a light-orange solid. MS m/z: 370.2 (M+H). Calc'd for C18H19N5O2S: 369.13.

Workup

  1. customprepared similar to
  2. temperatureThe reaction mixture was heated to reflux
  3. concentrationthen concentrated in vacuo
  4. washThe solid residue was washed with CH2Cl2 and EtOAc
  5. additionthe solid was diluted with MeOH
  6. concentrationconcentrated in vacuo
  7. additionThe residue was diluted with EtOAc
  8. washwashed with saturated NH4Cl and H2O
  9. dry with materialdried (MgSO4)
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-929a253c66754e338d0b874d18453ac0
Source dataset
uspto-grants-2007_03
Patent number
US07196104B2

Reaction notes

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