Ethanol → HCID 18771995, compound

HRID 479698Notes

Reaction equation

HRID 479698 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][CH2:31][OH:32].CC[O-].[Na+].CCO>CN(C=O)C>[CH2:31]([O:32][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]

Participants

5

Reactant 3

HCID 702EthanolHCID 18771586HCID 18771586, compoundHCID 23706232Ethanol sodium ethoxide2×

Product 1

HCID 18771995HCID 18771995, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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 EtOH (50 mL) was added a 21 wt % NaOEt/EtOH solution (0.4 mL, 1.2 mmol) and DMF (2 mL). The mixture was heated to reflux for 15 h then additional 21 wt % NaOEt/EtOH solution (10 mL) were added. After 2.5 h, the reaction was complete as judged by LC/MS. The reaction mixture was concentrated in vacuo then diluted with EtOAc and the solid was filtered off. The filtrate was concentrated in vacuo to afford an orange slushy oil which was purified by silica flash chromatography (5-10% MeOH/CH2Cl2) to afford the title compound as a yellow solid. MS m/z: 441.1 (M+H). Calc'd for C21H24N6O3S: 440.16.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 15 h
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. additionthen diluted with EtOAc
  5. filtrationthe solid was filtered off
  6. concentrationThe filtrate was concentrated in vacuo
  7. customto afford an orange slushy oil which
  8. customwas purified by silica flash chromatography (5-10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-bbd7caaf991c4ca48215a65736845561
Source dataset
uspto-grants-2003_11
Patent number
US06645990B2

Reaction notes

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