2-(3-Azabicyclo[3.1.0]hex-3-yl)-5-aminopyridine → N-[6-(3-Azabicyclo[3.1.0]hex-3-yl)-pyridin-3-yl]-5-fluoro-1-(3-fluorobenzyl)-1H-pyrrolo[2,3-b]pyridine-2-carboxamide

HRID 1019589Notes

Reaction equation

HRID 1019589 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[CH:10]=[C:9]([C:11]([OH:13])=O)[N:8]([CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=3)[C:5]2=[N:6][CH:7]=1.[CH:22]12[CH2:27][CH:26]1[CH2:25][N:24]([C:28]1[N:33]=[CH:32][C:31]([NH2:34])=[CH:30][CH:29]=1)[CH2:23]2>>[CH:26]12[CH2:27][CH:22]1[CH2:23][N:24]([C:28]1[N:33]=[CH:32][C:31]([NH:34][C:11]([C:9]3[N:8]([CH2:14][C:15]4[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=4)[C:5]4=[N:6][CH:7]=[C:2]([F:1])[CH:3]=[C:4]4[CH:10]=3)=[O:13])=[CH:30][CH:29]=1)[CH2:25]2

Participants

3

Reactant 2

HCID 574315312-(3-Azabicyclo[3.1.0]hex-3-yl)-5-aminopyridineHCID 669079435-Fluoro-1-(3-fluorobenzyl)-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid

Product 1

HCID 66908003N-[6-(3-Azabicyclo[3.1.0]hex-3-yl)-pyridin-3-yl]-5-fluoro-1-(3-fluorobenzyl)-1H-pyrrolo[2,3-b]pyridine-2-carboxamideYield 67.6%

Procedure

According to a method similar to that described in Stage 12.3, starting from 0.45 g (1.56 mmol) of 5-fluoro-1-[(3-fluorophenyl)methyl]-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid, described in the preceding stage, and 0.3 g (1.71 mmol) of 6-(3-azabicyclo[3.1.0]hex-3-yl)-3-aminopyridine, prepared in Stage 21.2, we obtain 0.47 g of the expected product.

Workup

  1. customprepared in Stage 21.2, we

Sources & evidence

ORD record
ord-92cdfdff9f834652ac8d6b19a9c39e4a
Source dataset
uspto-grants-2014_05
Patent number
US08716273B2

Reaction notes

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