1-(5-Chloro-6-(2,2-difluoroethoxy)pyridin-3-yl)ethanamine hydrochloride → 4-chloro-2-(1-(5-chloro-6-(2,2-difluoroethoxy)pyridin-3-yl)ethyl)-3-methyl-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-1-one

HRID 715249Notes

Reaction equation

HRID 715249 reaction equation
Br[CH:2]([C:4]1[C:13]([Cl:14])=[N:12][CH:11]=[CH:10][C:5]=1[C:6]([O:8]C)=O)[CH3:3].Cl.[Cl:16][C:17]1[CH:18]=[C:19]([CH:28]([NH2:30])[CH3:29])[CH:20]=[N:21][C:22]=1[O:23][CH2:24][CH:25]([F:27])[F:26]>>[Cl:14][C:13]1[C:4]2[CH:2]([CH3:3])[N:30]([CH:28]([C:19]3[CH:20]=[N:21][C:22]([O:23][CH2:24][CH:25]([F:26])[F:27])=[C:17]([Cl:16])[CH:18]=3)[CH3:29])[C:6](=[O:8])[C:5]=2[CH:10]=[CH:11][N:12]=1

Participants

3

Reactant 2

HCID 874267141-(5-Chloro-6-(2,2-difluoroethoxy)pyridin-3-yl)ethanamine hydrochlorideHCID 89875505Methyl 3-(1-bromoethyl)-2-chloroisonicotinate

Product 1

HCID 898744584-chloro-2-(1-(5-chloro-6-(2,2-difluoroethoxy)pyridin-3-yl)ethyl)-3-methyl-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-1-oneYield 17%

Procedure

The title compound is prepared in 17% yield (100 mg, colorless amorphous solid) from methyl 3-(1-bromoethyl)-2-chloroisonicotinate (400 mg, 1.4 mmol, Step-1 of Intermediate-6, racemate) and 1-(5-chloro-6-(2,2-difluoroethoxy)pyridin-3-yl)ethanamine hydrochloride (431 mg, 1.6 mmol, Amine-16, single enantiomer) in a similar manner to Intermediate-2.

Sources & evidence

ORD record
ord-b3128f602ada45ae9bf7c36325ab333e
Source dataset
uspto-grants-2015_11
Patent number
US09187475B2

Reaction notes

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