2-Methoxyethanol → HCID 18506778, compound

HRID 1355352Notes

Reaction equation

HRID 1355352 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][OH:5].[H-].[Na+].CS[C:10]1[N:11]=[N:12][C:13]([C:27]#[N:28])=[C:14]([N:16]2[CH2:22][CH2:21][C:20]3[CH:23]=[CH:24][CH:25]=[CH:26][C:19]=3[CH2:18][CH2:17]2)[N:15]=1>O1CCCC1>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:10]1[N:11]=[N:12][C:13]([C:27]#[N:28])=[C:14]([N:16]2[CH2:22][CH2:21][C:20]3[CH:23]=[CH:24][CH:25]=[CH:26][C:19]=3[CH2:18][CH2:17]2)[N:15]=1

Participants

5

Reactant 3

HCID 80192-MethoxyethanolHCID 24758Sodium hydrideHCID 18506776HCID 18506776, compound

Product 1

HCID 18506778HCID 18506778, compoundYield 9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under an argon atmosphere at 0° C., a solution of 25.6 mg (0.34 mmol) of 2-methoxy-ethanol in 2 ml of tetrahydrofurane was treated with 15 mg (0.34 mmol) of sodium hydride (55% dispersion in refined oil) and stirred during 15 min. To this mixture, a solution of 100 mg (0.34 mmol) of 3-methylsulfanyl-5-(1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-[1,2,4]triazine-6-carbonitrile in 3 ml of tetrahydrofurane was added and stirring continued for 18 h at 40° C. The yellow solution was evaporated under reduced pressure and the residue (141 mg) was chromatographed on silica gel with a 99:1 v/v mixture of dichloromethane and methanol as eluent. Thus were obtained 10 mg (9% of theory) of 3-(2-methoxy-ethoxy)-5-(1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-[1,2,4]triazine-6-carbonitrile as a light yellow solid; MS: 326 (M+H)+.

Workup

  1. stirringstirring
  2. waitcontinued for 18 h at 40° C
  3. customThe yellow solution was evaporated under reduced pressure
  4. customthe residue (141 mg) was chromatographed on silica gel with a 99:1 v/v mixture of dichloromethane and methanol as eluent

Sources & evidence

ORD record
ord-f470954a567a4bb3aa077e6ccaa5332b
Source dataset
uspto-grants-2003_07
Patent number
US06586422B2

Reaction notes

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