Sodium ethoxide → HCID 24898410, compound

HRID 2261197Notes

Reaction equation

HRID 2261197 reaction equation
[CH2:1]([NH:3][C:4]1[C:9]([CH:10]=O)=[CH:8][N:7]=[C:6]2[N:12](COC)[CH:13]=[C:14]([CH3:15])[C:5]=12)[CH3:2].[Cl:19][C:20]1[C:30]([CH2:31][C:32]#N)=[CH:29][C:28]([O:34][CH3:35])=[CH:27][C:21]=1[C:22]([NH:24][CH2:25][CH3:26])=[O:23].[O-:36]CC.[Na+]>CCO>[Cl:19][C:20]1[C:30]([C:31]2[C:32](=[O:36])[N:3]([CH2:1][CH3:2])[C:4]3[C:9](=[CH:8][N:7]=[C:6]4[NH:12][CH:13]=[C:14]([CH3:15])[C:5]4=3)[CH:10]=2)=[CH:29][C:28]([O:34][CH3:35])=[CH:27][C:21]=1[C:22]([NH:24][CH2:25][CH3:26])=[O:23]

Participants

5

Reactant 3

HCID 2723922Sodium ethoxideHCID 59198510HCID 59198510, compoundHCID 59198515HCID 59198515, compound

Product 1

HCID 24898410HCID 24898410, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 4-ethylamino-1-methoxymethyl-3-methyl-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde (10.9 mg, 0.044 mmole), 2-chloro-3-cyanomethyl-N-ethyl-5-methoxy-benzamide, anhydrous EtOH (0.2 ml) and sodium ethoxide (21% in EtOH, 0.4 mL) is heated at 120° C. on a oil bath for 4 h. The reaction solution is cooled to room temperature and quenched with sat. K2CO3. The mixture is extracted with chloroform/methanol (20:1) twice (2×15 mL). The extracts is washed with brine and dried over MgSO4. After removal of solvent, the residue is treated with acetic anhydride at 120° C. for 1 h. The solvent is removed and the residue is treated with HCl (6N, 1 mL) and heated at 100° C. for 2 h. The reaction mixture is cooled to room temperature and neutralized with solid K2CO3 to PH 11 and stirred at room temperature for 30 minutes. It is extracted with chloroform and methanol (20:1) and the extracts is combined and dried over MgSO4. After removal of the solvent, the residue is purified on silica gel column (Ethyl acetate:hexane=4:1) to give desired product. MS m/z 439.1 (M+1).

Workup

  1. temperatureThe reaction solution is cooled to room temperature
  2. customquenched with sat. K2CO3
  3. extractionThe mixture is extracted with chloroform/methanol (20:1) twice (2×15 mL)
  4. washThe extracts is washed with brine
  5. dry with materialdried over MgSO4
  6. customAfter removal of solvent
  7. additionthe residue is treated with acetic anhydride at 120° C. for 1 h
  8. customThe solvent is removed
  9. additionthe residue is treated with HCl (6N, 1 mL)
  10. temperatureheated at 100° C. for 2 h
  11. temperatureThe reaction mixture is cooled to room temperature and neutralized with solid K2CO3 to PH 11
  12. extractionIt is extracted with chloroform and methanol (20:1)
  13. dry with materialdried over MgSO4
  14. customAfter removal of the solvent
  15. customthe residue is purified on silica gel column (Ethyl acetate:hexane=4:1)

Sources & evidence

ORD record
ord-b863bc9cf1e1428681fe140f802f7e43
Source dataset
uspto-grants-2010_12
Patent number
US07846923B2

Reaction notes

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