Dimethylformamide → HCID 67158600, compound

HRID 549259Notes

Reaction equation

HRID 549259 reaction equation
[CH2:1]([NH:5][CH2:6][CH2:7][C:8]1[S:12][C:11]([CH3:13])=[N:10][C:9]=1[C:14]1[CH:34]=[CH:33][C:17]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][O:24][C:25]2[CH:32]=[CH:31][C:28]([C:29]#[N:30])=[CH:27][CH:26]=2)=[CH:16][CH:15]=1)[CH:2]([CH3:4])[CH3:3].CN(C)C=O.[C:40](Cl)(=[O:47])[C:41]1[CH:46]=[CH:45][CH:44]=[N:43][CH:42]=1.[H-].[Na+]>C(OCC)(=O)C.CO.CCCCCC>[CH2:1]([N:5]([C:40]([C:41]1[CH:42]=[N:43][CH:44]=[CH:45][CH:46]=1)=[O:47])[CH2:6][CH2:7][C:8]1[S:12][C:11]([CH3:13])=[N:10][C:9]=1[C:14]1[CH:15]=[CH:16][C:17]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][O:24][C:25]2[CH:26]=[CH:27][C:28]([C:29]#[N:30])=[CH:31][CH:32]=2)=[CH:33][CH:34]=1)[CH:2]([CH3:4])[CH3:3]

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 82604Nicotinoyl chlorideHCID 67157979HCID 67157979, compound

Product 1

HCID 67158600HCID 67158600, compoundYield 53%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

310 mg (0.65 mmol) of 4-(5-{4-[5-(2-isobutylaminoethyl)-2-methyl-thiazol-4-yl]phenoxy}pentyloxy)-benzonitrile compound (14b) obtained in Preparative Example 6-1 was added to 20 ml of dimethylformamide, and the mixture was cooled to 0°. To the mixture, 139 mg (0.78 mmol) of nicotinoyl chloride and 65 mg (1.62 mmol) of sodium hydride were added, and the mixture was stirred at room temperature 8 hrs. The reaction solution was diluted with ethyl acetate, and washed with purified water. The organic layer was dried over anhydrous magnesium sulfate, the solvent was removed therefrom, and the residue was purified by column chromatography using ethyl acetate:n-hexane:methanol=7:5:1 as an eluent to obtain 200 mg (yield: 53%) of a title compound (29).

Workup

  1. temperaturethe mixture was cooled to 0°
  2. washwashed with purified water
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customthe solvent was removed
  5. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-5de062a04cd042b39085dfdafde63c63
Source dataset
uspto-grants-2011_05
Patent number
US07943646B2

Reaction notes

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