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

HRID 715248Notes

Reaction equation

HRID 715248 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.[F:16][CH:17]([F:30])[CH2:18][O:19][C:20]1[N:25]=[CH:24][C:23]([CH:26]([NH2:28])[CH3:27])=[CH:22][C:21]=1[CH3:29]>>[Cl:14][C:13]1[C:4]2[CH:2]([CH3:3])[N:28]([CH:26]([C:23]3[CH:24]=[N:25][C:20]([O:19][CH2:18][CH:17]([F:30])[F:16])=[C:21]([CH3:29])[CH:22]=3)[CH3:27])[C:6](=[O:8])[C:5]=2[CH:10]=[CH:11][N:12]=1

Participants

3

Reactant 2

HCID 874263351-(6-(2,2-Difluoroethoxy)-5-methylpyridin-3-yl)ethanamine hydrochlorideHCID 89875505Methyl 3-(1-bromoethyl)-2-chloroisonicotinate

Product 1

HCID 898744944-chloro-2-(1-(6-(2,2-difluoroethoxy)-5-methylpyridin-3-yl)ethyl)-3-methyl-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-1-oneYield 24%

Procedure

The title compound is prepared in 24% yield (134 mg, colorless amorphous solid) from methyl 3-(1-bromoethyl)-2-chloroisonicotinate (400 mg, 1.4 mmol, Step-1 of Intermediate-6, racemate) and 1-(6-(2,2-difluoroethoxy)-5-methylpyridin-3-yl)ethanamine hydrochloride (399 mg, 1.6 mmol, Amine-5, single enantiomer) in a similar manner to Intermediate-2.

Sources & evidence

ORD record
ord-7afd4dde5e894dcdb8310bbed2361fc8
Source dataset
uspto-grants-2015_11
Patent number
US09187475B2

Reaction notes

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