Triethylamine → HCID 89874936, compound

HRID 715209Notes

Reaction equation

HRID 715209 reaction equation
Br[CH2:2][C:3]1[C:13]([Cl:14])=[N:12][CH:11]=[CH:10][C:4]=1[C:5]([O:7]CC)=O.Cl.[CH3:16][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].C(N(CC)CC)C>>[Cl:14][C:13]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]([CH3:16])[CH:18]=3)[CH3:30])[C:5](=[O:7])[C:4]=2[CH:10]=[CH:11][N:12]=1

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 675095881-(5-Methyl-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethanamine hydrochlorideHCID 89874240Ethyl 3-(bromomethyl)-2-chloroisonicotinate

Product 1

HCID 89874936HCID 89874936, compoundYield 78%

Procedure

The title compound is prepared in 78% yield (540 mg, pale yellow solid) from ethyl 3-(bromomethyl)-2-chloroisonicotinate (500 mg, 1.8 mmol, Step-1 of Intermediate-1), 1-(5-methyl-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethanamine hydrochloride (490 mg, 1.8 mmol, Amine-2, single enantiomer), and triethylamine (1.0 mL, 7.2 mmol) as a base in a similar manner to Step-2 of Intermediate-1.

Sources & evidence

ORD record
ord-2292f71e71af4ddc85c12d0e6f2cd1d0
Source dataset
uspto-grants-2015_11
Patent number
US09187475B2

Reaction notes

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