Thionyl Chloride → 6-[(3-Cyclobutyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)oxy]-3-pyridinecarbohydrazide

HRID 222667Notes

Reaction equation

S(Cl)(Cl)=O.[CH:5]1([N:9]2[CH2:15][CH2:14][C:13]3[CH:16]=[CH:17][C:18]([O:20][C:21]4[N:26]=[CH:25][C:24]([C:27]([OH:29])=O)=[CH:23][CH:22]=4)=[CH:19][C:12]=3[CH2:11][CH2:10]2)[CH2:8][CH2:7][CH2:6]1.O.[NH2:31][NH2:32]>O1CCCC1.C(OCC)(=O)C>[CH:5]1([N:9]2[CH2:15][CH2:14][C:13]3[CH:16]=[CH:17][C:18]([O:20][C:21]4[N:26]=[CH:25][C:24]([C:27]([NH:31][NH2:32])=[O:29])=[CH:23][CH:22]=4)=[CH:19][C:12]=3[CH2:11][CH2:10]2)[CH2:6][CH2:7][CH2:8]1

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of thionyl chloride (2 ml) and 6-[(3-cyclobutyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)oxy]-3-pyridinecarboxylic acid (E196b) (200 mg, 0.59 mmol) was stirred at reflux for 1 hour. The reaction mixture was concentrated in vacuo to afford a crude residue. The residue was dissolved in tetrahydrofuran (5 ml), cooled to 0° C. and hydrazine hydrate (1.5 ml) in tetrahydrofuran (1.5 ml) was added dropwise. The reaction mixture was allowed to warm to room temperature and stirred for 1 hour. The reaction mixture was then diluted with ethyl acetate and washed with a saturated solution of sodium carbonate, water, brine and dried (magnesium sulfate). The organic layer was filtered and concentrated in vacuo to afford the title compound (D54); MS (ES+) m/e 361 [M+H]+.

Workup

temperatureat reflux for 1 hour
concentrationThe reaction mixture was concentrated in vacuo
customto afford a crude residue
temperatureto warm to room temperature
stirringstirred for 1 hour
washwashed with a saturated solution of sodium carbonate, water, brine
dry with materialdried (magnesium sulfate)
filtrationThe organic layer was filtered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-d1dcca1c858d476990fb25c14c32a209
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08207331B2

Reaction notes

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