Water → HCID 67042545, compound

HRID 1915066Notes

Reaction equation

HRID 1915066 reaction equation
[NH2:1][C:2]1[CH:23]=[CH:22][C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]([C:13]3[CH:14]=[C:15]([C:18]([O:20][CH3:21])=[O:19])[S:16][CH:17]=3)[CH:8]=2)=[CH:4][CH:3]=1.[F:24][C:25]1[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][C:26]=1[N:32]=[C:33]=[O:34].O>C1COCC1>[F:24][C:25]1[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][C:26]=1[NH:32][C:33]([NH:1][C:2]1[CH:23]=[CH:22][C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]([C:13]3[CH:14]=[C:15]([C:18]([O:20][CH3:21])=[O:19])[S:16][CH:17]=3)[CH:8]=2)=[CH:4][CH:3]=1)=[O:34]

Participants

5

Reactant 3

HCID 962WaterHCID 27333772-Fluoro-5-methylphenyl isocyanateHCID 58167941HCID 58167941, compound

Product 1

HCID 67042545HCID 67042545, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of methyl 4-[4-(4-aminophenoxy)pyridin-2-yl]thiophene-2-carboxylate (500 mg, 1.53 mmol) in anhydrous THF (10 ml) was added 2-fluoro-5-methyl-phenylisocyanate (255 mg, 1.68 mmol). The mixture was stirred at room temperature for one hour and poured into 200 ml of water. The resulting precipitates were filtered, washed with water and dried in vacuo to give the crude, which was purified by silica gel chromatography eluting with 3-5% MeOH/CHCl3 to give methyl 4-{4-[4-({[(2-fluoro-5-methylphenyl)amino]carbonyl}amino)phenoxy]pyridin-2-yl}thiophene-2-carboxylate as off-white solid. Yield: 560 mg, 76%.

Workup

  1. customThe resulting precipitates
  2. filtrationwere filtered
  3. washwashed with water
  4. customdried in vacuo
  5. customto give the crude, which
  6. customwas purified by silica gel chromatography
  7. washeluting with 3-5% MeOH/CHCl3

Sources & evidence

ORD record
ord-95899cf1bf0841f0aee21f087e02654f
Source dataset
uspto-grants-2013_12
Patent number
US08614234B2

Reaction notes

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