Water → HCID 22734210, compound

HRID 2084789Notes

Reaction equation

HRID 2084789 reaction equation
[C:1]([CH2:4][C:5]1[C:9]2[C:10]([C:16](=[O:26])[CH2:17][C:18]3[C:23]([Cl:24])=[CH:22][N:21]=[CH:20][C:19]=3[Cl:25])=[CH:11][CH:12]=[C:13]([O:14][CH3:15])[C:8]=2[O:7][CH:6]=1)(O)=[O:2].C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:39][CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][N:42]=1.O>C(#N)C>[Cl:25][C:19]1[CH:20]=[N:21][CH:22]=[C:23]([Cl:24])[C:18]=1[CH2:17][C:16]([C:10]1[C:9]2[C:5]([CH2:4][C:1]([NH:39][CH2:40][C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][N:42]=3)=[O:2])=[CH:6][O:7][C:8]=2[C:13]([O:14][CH3:15])=[CH:12][CH:11]=1)=[O:26]

Participants

6

Reactant 4

HCID 962WaterHCID 195092-PyridinemethanamineHCID 682631,1'-CarbonyldiimidazoleHCID 22733964HCID 22733964, compound

Product 1

HCID 22734210HCID 22734210, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

Compound 151 (0.15 g) obtained in Example 151 was dissolved in acetonitrile (3.0 ml), and carbonyldiimidazole (0.086 g) was added thereto under ice-cooling, followed by stirring at 60° C. for 30 minutes. 2-(Aminomethyl)pyridine (0.050 ml) was added to the mixture at room temperature followed by stirring for one hour. Water was added to the mixture and a precipitate was collected by filtration. The obtained crystals were recrystallized from DMF/water to give 4-[2-(3,5-dichloro-4-pyridyl)-1-oxoethyl]-7-methoxy-3-[(2-pyridylmethyl)aminocarbonylmethyl]benzofuran (0.13 g, 68%) as white crystals. Then, substantially the same procedure as in Example 51 was repeated using the obtained crystals to give Compound 157.

Workup

  1. temperatureunder ice-cooling
  2. stirringby stirring for one hour
  3. filtrationa precipitate was collected by filtration
  4. customThe obtained crystals were recrystallized from DMF/water

Sources & evidence

ORD record
ord-d7071b8f4445460fa4d55209db00678c
Source dataset
uspto-grants-2004_04
Patent number
US06716987B1

Reaction notes

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