Methanol → HCID 18771618, compound

HRID 479699Notes

Reaction equation

HRID 479699 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][N:24]4[CH2:29][CH2:28][O:27][CH2:26][CH2:25]4)[N:18]=3)=[O:15])[N:12]=2)[CH:5]=[CH:4][N:3]=1.[CH3:30][OH:31].C[O-].[Na+]>CN(C=O)C>[CH3:30][O:31][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][N:24]4[CH2:29][CH2:28][O:27][CH2:26][CH2:25]4)[N:18]=3)=[O:15])[N:12]=2)[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 10942334Sodium MethoxideHCID 18771586HCID 18771586, compound

Product 1

HCID 18771618HCID 18771618, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

To a mixture of 1-[2-(2-chloropyridin-4-yl)thiazol-4-yl]-3-(6-morpholin-4-ylmethyl-pyridin-2-yl)urea (100 mg, 0.23 mmol, Example 90) and MeOH (50 mL) was added solid NaOMe (1.6 g, 29.6 mmol) and DMF (20 mL). The reaction mixture was heated to 130° C. After 2 h, the reaction mixture was cooled to RT and filtered. The filtrate was concentrated in vacuo and diluted with EtOAc and filtered to remove the solid. The filtrate was concentrated in vacuo to afford an orange oil which was purified by silica flash chromatography (5% MeOH/CH2Cl2) to afford the title compound as a white solid. MS m/z: 427.2 (M+H). Calc'd for C20H22N6O3S: 426.15.

Workup

  1. temperaturethe reaction mixture was cooled to RT
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated in vacuo
  4. additiondiluted with EtOAc
  5. filtrationfiltered
  6. customto remove the solid
  7. concentrationThe filtrate was concentrated in vacuo
  8. customto afford an orange oil which
  9. customwas purified by silica flash chromatography (5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-f0e7d095f43840769c2802b60b5f3755
Source dataset
uspto-grants-2003_11
Patent number
US06645990B2

Reaction notes

Loading…