6-(3-Azabicyclo[3.2.0]hept-3-yl)-3-aminopyridine → N-[6-(3-Azabicyclo[3.2.0]hept-3-yl)pyridin-3-yl]-5-trifluoromethyl-1-(3-fluorobenzyl)-1H-pyrrolo[2,3-b]pyridine-2-carboxamide

HRID 1019552Notes

Reaction equation

HRID 1019552 reaction equation
[F:1][C:2]([F:24])([F:23])[C:3]1[CH:4]=[C:5]2[CH:11]=[C:10]([C:12]([OH:14])=O)[N:9]([CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=3)[C:6]2=[N:7][CH:8]=1.[CH:25]12[CH2:31][CH2:30][CH:29]1[CH2:28][N:27]([C:32]1[N:37]=[CH:36][C:35]([NH2:38])=[CH:34][CH:33]=1)[CH2:26]2>>[CH:29]12[CH2:30][CH2:31][CH:25]1[CH2:26][N:27]([C:32]1[N:37]=[CH:36][C:35]([NH:38][C:12]([C:10]3[N:9]([CH2:15][C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=4)[C:6]4=[N:7][CH:8]=[C:3]([C:2]([F:23])([F:1])[F:24])[CH:4]=[C:5]4[CH:11]=3)=[O:14])=[CH:34][CH:33]=1)[CH2:28]2

Participants

3

Reactant 2

HCID 591900896-(3-Azabicyclo[3.2.0]hept-3-yl)-3-aminopyridineHCID 668635175-Trifluoromethyl-1-[(3-fluorophenyl)methyl]-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid

Product 1

HCID 66907778N-[6-(3-Azabicyclo[3.2.0]hept-3-yl)pyridin-3-yl]-5-trifluoromethyl-1-(3-fluorobenzyl)-1H-pyrrolo[2,3-b]pyridine-2-carboxamideYield 67.3%

Procedure

According to a method similar to that described in Stage 12.3, starting from 0.12 g (0.35 mmol) of 5-trifluoromethyl-1-[(3-fluorophenyl)methyl]-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid, described in Stage 1.3, and 0.075 g (0.38 mmol) of 6-(3-azabicyclo[3.2.0]hept-3-yl)-3-aminopyridine, prepared in the preceding stage, we obtain 0.12 g of the expected product.

Workup

  1. customprepared in the preceding stage, we

Sources & evidence

ORD record
ord-df03ad97f1334218959dba705cb8dacf
Source dataset
uspto-grants-2014_05
Patent number
US08716272B2

Reaction notes

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