HCID 23654464, compound → HCID 23654010, compound

HRID 597953Notes

Reaction equation

HRID 597953 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([O:21][CH3:22])[C:6]2[CH2:12][CH2:11][N:10](C(OC(C)(C)C)=O)[CH2:9][CH2:8][C:7]=2[N:20]=1>Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([O:21][CH3:22])[C:6]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8][C:7]=2[N:20]=1

Participants

3

Reactant 1

HCID 23654464HCID 23654464, compound

Product 1

HCID 23654010HCID 23654010, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Ag2CO3 (1.63 mmol, 449 mg) was added to a solution of tert-butyl 4-hydroxy-2-oxo-1,2,5,6,8,9-hexahydro-7H-pyrido[2,3-d]azepine-7-carboxylate (91.0 mg, 0.325 mmol) in DCM (1.5 ml) at room temperature. After 10 min of stirring, MeI (1.63 mmol, 106 μl) was added. After 15 h of stirring, sat. aq. NH4Cl was added and the mixture was extracted with DCM. The organic layer was washed with water, dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified by column chromatography to provide 72 mg (72%) of tert-butyl 2,4-dimethoxy-5,6,8,9-tetrahydro-7H-pyrido[2,3-d]azepine-7-carboxylate. 1H-NMR (CDCl3) δ 6.02 (1H), 3.85 (3H), 3.76 (3H), 3.55 (2H), 3.48 (2H), 2.98 (2H), 2.81 (2H), 1.45 (9H) ppm. tert-Butyl 2,4-dimethoxy-5,6,8,9-tetrahydro-7H-pyrido[2,3-d]azepine-7-carboxylate (72 mg, 0.23 mmol) was dissolved in HCl (2 N in Et2O, 3 ml) and stirred for 16 h at room temperature. The hydrochloric salt of 2,4-dimethoxy-6,7,8,9-tetrahydro-5H-pyrido[2,3-d]azepine was obtained in quantitative yield. 1H-NMR (CDCl3) δ 9.98 (br s, 2H), 6.32 (s, 1H), 3.73 (s, 3H), 3.65 (s, 3H), 3.25 (m, 2H), 2.88 (m, 2H), 2.86 (m, 2H), 2.78 (m, 2H) ppm.

Sources & evidence

ORD record
ord-48cb7b60cc5c44cba62ea407430b3f0c
Source dataset
uspto-grants-2011_03
Patent number
US07897595B2

Reaction notes

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