Cyclohexylamine → Ethyl 6-bromo-1-cyclohexyl-4-oxo-1,4-dihydro-1,7-naphthyridine-3-carboxylate

HRID 1047165Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([C:17](F)=[CH:18][N:19]=1)[C:5]([C:7](=[CH:13][N:14]([CH3:16])C)[C:8]([O:10][CH2:11][CH3:12])=[O:9])=[O:6].[CH:21]1(N)[CH2:26][CH2:25]C[CH2:23][CH2:22]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:17](=[CH:18][N:19]=1)[N:14]([CH:16]1[CH2:25][CH2:26][CH2:21][CH2:22][CH2:23]1)[CH:13]=[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:5]2=[O:6]

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of ethyl 2-(2-bromo-5-fluoroisonicotinoyl)-3-(dimethylamino)acrylate (Intermediate 66, 1.14 g, 3.29 mmol, 1 equiv.) in DMF (6.5 mL) was added cyclohexanamine (592 mg, 3.29 mmol, 1 equiv.). This reaction mixture was stirred at 70° C. for 30 min. Potassium carbonate (1.36 g, 9.86 mmol, 3 equiv.) was added and stirred at 70° C. for 2 h. The reaction mixture was cooled to room temperature and quenched with water (2 mL). 1 N HCl was added until pH 4-5 was reached. The precipitate was washed with water and hexanes and dried to provide ethyl 6-bromo-1-cyclohexyl-4-oxo-1,4-dihydro-1,7-naphthyridine-3-carboxylate (1.15 g, 92%).

Workup

stirringstirred at 70° C. for 2 h
temperatureThe reaction mixture was cooled to room temperature
customquenched with water (2 mL)
addition1 N HCl was added until pH 4-5
washThe precipitate was washed with water and hexanes
customdried

Sources & evidence

ORD record: ord-f62859f6eb9149b6a0dcad80d82be1b4
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08569484B2

Reaction notes

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