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

HRID 715241Notes

Reaction equation

HRID 715241 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:29])[CH2:18][O:19][C:20]1[N:25]=[CH:24][C:23]([CH2:26][NH2:27])=[CH:22][C:21]=1[CH3:28]>>[Cl:14][C:13]1[C:4]2[CH:2]([CH3:3])[N:27]([CH2:26][C:23]3[CH:24]=[N:25][C:20]([O:19][CH2:18][CH:17]([F:29])[F:16])=[C:21]([CH3:28])[CH:22]=3)[C:6](=[O:8])[C:5]=2[CH:10]=[CH:11][N:12]=1

Participants

3

Reactant 2

HCID 87426846(6-(2,2-Difluoroethoxy)-5-methylpyridin-3-yl)methanamine hydrochlorideHCID 89875505Methyl 3-(1-bromoethyl)-2-chloroisonicotinate

Product 1

HCID 898742204-chloro-2-((6-(2,2-difluoroethoxy)-5-methylpyridin-3-yl)methyl)-3-methyl-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-1-oneYield 24%

Procedure

The title compound is prepared in 24% yield (63 mg, colorless oil) from methyl 3-(1-bromoethyl)-2-chloroisonicotinate (200 mg, 0.72 mmol, Step-1 of Intermediate-6, racemate) and (6-(2,2-difluoroethoxy)-5-methylpyridin-3-yl)methanamine hydrochloride (206 mg, 0.86 mmol, Amine-4) in a similar manner to Intermediate-2.

Sources & evidence

ORD record
ord-f375d9f67a0b4f89b1b8fb3e1719df04
Source dataset
uspto-grants-2015_11
Patent number
US09187475B2

Reaction notes

Loading…