3-Fluoro-N,N-dimethylpyridine-2,5-diamine → N-[5-Fluoro-6-(N,N-dimethylamino)pyridin-3-yl]-5-trifluoromethyl-1-(3-fluorobenzyl)-1H-pyrrolo[2,3-b]pyridine-2-carboxamide

HRID 1019547Notes

Reaction equation

HRID 1019547 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH2:11])[CH:5]=[N:6][C:7]=1[N:8]([CH3:10])[CH3:9].[F:12][C:13]([F:35])([F:34])[C:14]1[CH:15]=[C:16]2[CH:22]=[C:21]([C:23](O)=[O:24])[N:20]([CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([F:33])[CH:28]=3)[C:17]2=[N:18][CH:19]=1>>[F:1][C:2]1[CH:3]=[C:4]([NH:11][C:23]([C:21]2[N:20]([CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([F:33])[CH:28]=3)[C:17]3=[N:18][CH:19]=[C:14]([C:13]([F:12])([F:35])[F:34])[CH:15]=[C:16]3[CH:22]=2)=[O:24])[CH:5]=[N:6][C:7]=1[N:8]([CH3:9])[CH3:10]

Participants

3

Reactant 2

HCID 451219193-Fluoro-N,N-dimethylpyridine-2,5-diamineHCID 668635175-Trifluoromethyl-1-[(3-fluorophenyl)methyl]-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid

Product 1

HCID 66907497N-[5-Fluoro-6-(N,N-dimethylamino)pyridin-3-yl]-5-trifluoromethyl-1-(3-fluorobenzyl)-1H-pyrrolo[2,3-b]pyridine-2-carboxamideYield 385.6%

Procedure

Compound No. 35 was prepared by a method similar to that described in Stage 1.4 by reacting 0.4 g (1.18 mmol) of 5-fluoro-6-(N,N-dimethylamino)-3-aminopyridine (WO2004/110986), with 0.4 g (0.18 mmol) of 5-trifluoromethyl-1-[(3-fluorophenyl)methyl]-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid obtained in Stage 1.3. We thus obtain 0.33 g of the expected product in the form of a solid.

Workup

  1. custom35 was prepared by a method similar to

Sources & evidence

ORD record
ord-1a4b263db2744d4da76dde89e6af871b
Source dataset
uspto-grants-2014_05
Patent number
US08716272B2

Reaction notes

Loading…