Dimethylamine → HCID 10983023, compound

HRID 1017222Notes

Reaction equation

HRID 1017222 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′-carbonyidiimidazole (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-b1c58cdeffaa470b9eebefe9a5d8d765
Source dataset
uspto-grants-2002_11
Patent number
US06479485B2

Reaction notes

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