Dimethylamine → HCID 10983023, compound

HRID 2295089Notes

Reaction equation

HRID 2295089 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:28]=[CH:29][CH:30]=1)[O:6][C:7]1[N:12]=[C:11]([O:13][C:14]2[CH:15]=C([CH:20]=[CH:21][C:22]=2[O:23][CH3:24])C(O)=O)[C:10]([F:25])=[C:9]([CH3:26])[C:8]=1[F:27])#[N:2].[C:31]([N:38]1[CH:42]=[CH:41]N=[CH:39]1)(N1C=CN=C1)=O.CNC.[O:46]1CCCC1>>[C:1]([C:3]1[CH:4]=[C:5]([CH:28]=[CH:29][CH:30]=1)[O:6][C:7]1[N:12]=[C:11]([O:13][C:14]2[CH:15]=[C:41]([CH:20]=[CH:21][C:22]=2[O:23][CH3:24])[C:42]([N:38]([CH3:31])[CH3:39])=[O:46])[C:10]([F:25])=[C:9]([CH3:26])[C:8]=1[F:27])#[N:2]

Participants

5

Reactant 4

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 682631,1'-CarbonyldiimidazoleHCID 23441835HCID 23441835, compound

Product 1

HCID 10983023HCID 10983023, compound

Procedure

To 3-[(6-(3-cyanophenoxy)-3,5-difluoro-4-methylpyridin-2-yl)oxy]-4-methoxybenzoic acid (0.47 g, 1.1 mmol) in tetrahydrofuran (12 mL) was added 1,1'-carbonyldiimidazole (0.22 g, 1.4 mmol) and stirred at ambient temperature for 3 hours. Then dimethylamine (aq, 0.077 g, 1.7 mmol) was added. After stirring for 12 hours the solution was partitioned between water and ethyl acetate. The organic layer was separated, dried (MgSO4), and the solvent was removed in vacuo. Chromatography on silica gel with ethyl acetate/hexane (1/8) as eluent gave 3-[(6-(3-cyanophenoxy)-3,5-difluoro-4-methylpyridin-2-yl)oxy]-N,N-dimethyl-4-methoxybenzamide; NMR (CDCl3) 6.9-7.4 (m,7), 3.8 (s,3), 3.0 (br,6), 2.4 (s,3) ppm.

Workup

  1. stirringAfter stirring for 12 hours the solution
  2. customwas partitioned between water and ethyl acetate
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-9e36d9be0758410f95de00e844455b11
Source dataset
uspto-grants-1997_11
Patent number
US05691364

Reaction notes

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