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

HRID 715217Notes

Reaction equation

HRID 715217 reaction equation
Br[CH2:2][C:3]1[C:12]([Cl:13])=[N:11][CH:10]=[CH:9][C:4]=1[C:5]([O:7]C)=O.Cl.[CH3:15][O:16][C:17]1[CH:18]=[C:19]([CH:29]([NH2:31])[CH3:30])[CH:20]=[N:21][C:22]=1[O:23][CH2:24][C:25]([F:28])([F:27])[F:26]>>[Cl:13][C:12]1[C:3]2[CH2:2][N:31]([CH:29]([C:19]3[CH:20]=[N:21][C:22]([O:23][CH2:24][C:25]([F:28])([F:26])[F:27])=[C:17]([O:16][CH3:15])[CH:18]=3)[CH3:30])[C:5](=[O:7])[C:4]=2[CH:9]=[CH:10][N:11]=1

Participants

3

Reactant 2

HCID 675084391-(5-Methoxy-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethanamine hydrochlorideHCID 72213786Methyl 3-(bromomethyl)-2-chloropyridine-4-carboxylate

Product 1

HCID 898752094-chloro-2-(1-(5-methoxy-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethyl)-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-1-oneYield 61%

Procedure

The title compound is prepared in 61% yield (140 mg, colorless amorphous solid) from methyl 3-(bromomethyl)-2-chloroisonicotinate (150 mg, 0.57 mmol) and 1-(5-methoxy-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethanamine hydrochloride (163 mg, 0.57 mmol, Amine-9, single enantiomer) in a similar manner to Intermediate-2.

Sources & evidence

ORD record
ord-2d0975a3771740fbb2340eb6732e68aa
Source dataset
uspto-grants-2015_11
Patent number
US09187475B2

Reaction notes

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