Dimethylamine → N-[2-(N,N-Dimethylamino)pyrimidin-5-yl]-5-trifluoromethyl-1-(3-fluorobenzyl)-1H-pyrrolo[2,3-b]pyridine-2-carboxamide

HRID 1019549Notes

Reaction equation

HRID 1019549 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[N:23]([CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[CH:26]=3)[C:14]3=[N:15][CH:16]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:18]=[C:13]3[CH:12]=2)=[O:10])=[CH:4][N:3]=1.[CH3:32][NH:33][CH3:34]>C(O)C>[CH3:32][N:33]([C:2]1[N:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[N:23]([CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[CH:26]=3)[C:14]3=[N:15][CH:16]=[C:17]([C:19]([F:20])([F:21])[F:22])[CH:18]=[C:13]3[CH:12]=2)=[O:10])=[CH:4][N:3]=1)[CH3:34]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 86639061N-(2-Chloropyrimidin-5-yl)-5-trifluoromethyl-1-(3-fluorobenzyl)-1H-pyrrolo[2,3-b]pyridine-2-carboxamide

Product 1

HCID 66907511N-[2-(N,N-Dimethylamino)pyrimidin-5-yl]-5-trifluoromethyl-1-(3-fluorobenzyl)-1H-pyrrolo[2,3-b]pyridine-2-carboxamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a sealed tube, a mixture of 0.2 g (0.44 mmol) of N-(2-chloropyrimidin-5-yl)-5-trifluoromethyl-1-(3-fluorobenzyl)-1H-pyrrolo[2,3-b]pyridine-2-carboxamide, prepared in the preceding stage, and 1.3 mL (8.89 mmol) of an aqueous solution of dimethylamine at 40%, the whole in solution in 15 mL of ethanol, is heated at 110° C. for 20 h. After this time, the reaction mixture is allowed to return to room temperature, then a white precipitate is collected by filtration, washed with water and dried at reduced pressure to obtain 0.14 g of the expected product.

Workup

  1. customto return to room temperature
  2. filtrationa white precipitate is collected by filtration
  3. washwashed with water
  4. customdried at reduced pressure

Sources & evidence

ORD record
ord-8aaf773b5bca41f9b255ef35e2a1990f
Source dataset
uspto-grants-2014_05
Patent number
US08716272B2

Reaction notes

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