Water → HCID 117600654, compound

HRID 1497732Notes

Reaction equation

HRID 1497732 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([NH2:8])=[C:4]([CH:9]([NH:16][CH3:17])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:3]=1.[C:18](N1C=CN=C1)(N1C=CN=C1)=O.[OH2:30]>C1COCC1>[Cl:1][C:2]1[N:7]=[CH:6][C:5]2[NH:8][C:17](=[O:30])[N:16]([CH3:18])[CH:9]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 682631,1'-CarbonyldiimidazoleHCID 117600859HCID 117600859, compound

Product 1

HCID 117600654HCID 117600654, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6-Chloro-4-(methylamino-phenyl-methyl)-pyridin-3-ylamine (100 mg, 0.323 mmol) and 1,1′-carbonyl-diimidazole (100 mg, 0.586 mmol) are stirred in THF (5 mL) at room temperature for 1.5 hours. The reaction mixture is added to water and the aqueous phase extracted with dichloromethane. The organic phase is dried over magnesium sulfate. The solvent is removed in vacuo and the residue purified by column chromatography on silica gel using a dichloromethane/methanol gradient. The product fractions are evaporated to dryness to provide the desired compound.

Workup

  1. extractionthe aqueous phase extracted with dichloromethane
  2. dry with materialThe organic phase is dried over magnesium sulfate
  3. customThe solvent is removed in vacuo
  4. customthe residue purified by column chromatography on silica gel using a dichloromethane/methanol gradient
  5. customThe product fractions are evaporated to dryness

Sources & evidence

ORD record
ord-ab6b11a6dade4df8a60cd43e9a337992
Source dataset
uspto-grants-2015_12
Patent number
US09199988B2

Reaction notes

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