(2R)-1,1,1-trifluoro-3-methylbutan-2-amine → 9-bromo-1-chloro-N-[(1R)-2-methyl-1-(trifluoromethyl)propyl]benzo[c]-1,6-naphthyridin-6-amine

HRID 2192961Notes

Reaction equation

[Br:1][C:2]1[CH:17]=[CH:16][C:5]2[C:6](Cl)=[N:7][C:8]3[C:13]([C:4]=2[CH:3]=1)=[C:12]([Cl:14])[N:11]=[CH:10][CH:9]=3.[F:18][C:19]([F:26])([F:25])[C@H:20]([NH2:24])[CH:21]([CH3:23])[CH3:22]>O1CCOCC1>[Br:1][C:2]1[CH:17]=[CH:16][C:5]2[C:6]([NH:24][C@@H:20]([C:19]([F:26])([F:25])[F:18])[CH:21]([CH3:23])[CH3:22])=[N:7][C:8]3[C:13]([C:4]=2[CH:3]=1)=[C:12]([Cl:14])[N:11]=[CH:10][CH:9]=3

Participants

Conditions

Temperature: 150 °C

Procedure

To a solution of dried 9-bromo-1,6-dichlorobenzo[c]-1,6-naphthyridine (0.80 g, 2.46 mmol) in dioxane (16 mL) was added (2R)-1,1,1-trifluoro-3-methylbutan-2-amine (2.4 g, 17.2 mmol) and heated to 150° C. for 24-48 hrs. The reaction was concentrated to dryness to give 9-bromo-1-chloro-N-[(1R)-2-methyl-1-(trifluoromethyl)propyl]benzo[c]-1,6-naphthyridin-6-amine. LRMS (ESI) calc'd for (C17H15BrClF3N3) [M+H]+, 432.0; found 432.0.

Workup

concentrationThe reaction was concentrated to dryness

Sources & evidence

ORD record: ord-ab350e9e1cfd4f7882bee4dcac713165
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08329722B2

Reaction notes

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