Acetic Acid → N-{2-[(3-Cyclobutyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)oxy]-1,3-thiazol-5-yl}acetamide

HRID 645844Notes

Reaction equation

[CH:1]1([N:5]2[CH2:11][CH2:10][C:9]3[CH:12]=[CH:13][C:14]([O:16][C:17]4[S:18][C:19]([N+:22]([O-])=O)=[CH:20][N:21]=4)=[CH:15][C:8]=3[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1.C(=O)(O)[O-].[Na+].[C:30](O)(=[O:32])[CH3:31]>C(OC(=O)C)(=O)C.[Fe]>[CH:1]1([N:5]2[CH2:11][CH2:10][C:9]3[CH:12]=[CH:13][C:14]([O:16][C:17]4[S:18][C:19]([NH:22][C:30](=[O:32])[CH3:31])=[CH:20][N:21]=4)=[CH:15][C:8]=3[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: 80 °C

Procedure

Iron powder (162 mg, 2.9 mmol) was added to a stirred solution of 3-cyclobutyl-7-[(5-nitro-1,3-thiazol-2-yl)oxy]-2,3,4,5-tetrahydro-1H-3-benzazepine (E210a) (162 mg, 0.47 mmol) in acetic acid (1 ml) and acetic anhydride (1 ml). The reaction mixture was stirred at 80° C. for 16 hours then cooled and poured onto ice. The solution was basified to pH 8 (sodium bicarbonate) and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried (sodium sulfate). Concentration in vacuo and subsequent purification of the resulting residue by column chromatography eluting with a mixture of 0.880 ammonia:methanol:dichloromethane (0.3:2.7:97) afforded the title compound (E210). MS (ES+) m/e 358 [M+H]+.

Workup

temperaturethen cooled
additionpoured onto ice
extractionthe resulting mixture was extracted with ethyl acetate
washThe organic layer was washed with brine
dry with materialdried (sodium sulfate)
concentrationConcentration
customin vacuo and subsequent purification of the resulting residue by column chromatography
washeluting with a mixture of 0.880 ammonia:methanol:dichloromethane (0.3:2.7:97)

Sources & evidence

ORD record: ord-cc11ccceeb42401ca310f03f0bf5e099
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07704994B2

Reaction notes

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