Dimethylamine → HCID 10983023, compound

HRID 2119515Notes

Reaction equation

HRID 2119515 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-methypyridin-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-1d8bb82df30747238197a29577f5711b
Source dataset
uspto-grants-2004_02
Patent number
US06686364B2

Reaction notes

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