Water → HCID 86725300, compound

HRID 1403234Notes

Reaction equation

HRID 1403234 reaction equation
[I:1]N1C(=O)CCC1=O.[Cl:9][C:10]1[CH:11]=[CH:12][C:13]([CH3:32])=[C:14]([C:16]2[NH:17][C:18]([C:24]3[CH:29]=[CH:28][N:27]=[C:26]([NH:30][CH3:31])[N:25]=3)=[CH:19][C:20]=2[C:21]([NH2:23])=[O:22])[CH:15]=1.O>CN(C=O)C>[Cl:9][C:10]1[CH:11]=[CH:12][C:13]([CH3:32])=[C:14]([C:16]2[NH:17][C:18]([C:24]3[CH:29]=[CH:28][N:27]=[C:26]([NH:30][CH3:31])[N:25]=3)=[C:19]([I:1])[C:20]=2[C:21]([NH2:23])=[O:22])[CH:15]=1

Participants

5

Reactant 3

HCID 962WaterHCID 120273N-IodosuccinimideHCID 66571316HCID 66571316, compound

Product 1

HCID 86725300HCID 86725300, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-iodosuccinimide (301 mg, 1.34 mmol) was added to a solution of 2-(5-chloro-2-methylphenyl)-5-[2-(methylamino)pyrimidin-4-yl]-1H-pyrrole-3-carboxamide (433 mg, 1.27 mmol) in dry DMF (5 mL). The reaction mixture was stirred at room temperature for 5 h and poured into iced water (50 mL). The solid was then filtered with suction, washed thoroughly with water, dried in an oven under vacuum at 50° C. and purified by flash chromatography over silica gel (DCM/MeOH/7 N NH3 in MeOH 95/5/0.5) to afford the title compound (344 mg, 58%).

Workup

  1. filtrationThe solid was then filtered with suction
  2. washwashed thoroughly with water
  3. customdried in an oven under vacuum at 50° C.
  4. custompurified by flash chromatography over silica gel (DCM/MeOH/7 N NH3 in MeOH 95/5/0.5)

Sources & evidence

ORD record
ord-7ed0a7b1130548628c2039e642978f20
Source dataset
uspto-grants-2014_12
Patent number
US08912200B2

Reaction notes

Loading…