Hydrochloric Acid → HCID 22645207, compound

HRID 2414419Notes

Reaction equation

[Cl:1][C:2]1C=[C:6]([N:8]2[CH2:13][CH2:12][CH:11]([C:14]([O:16]CC)=O)[CH2:10][CH2:9]2)[CH:5]=[CH:4][N:3]=1.Cl.Cl.[NH2:21][CH2:22][CH2:23][O:24][C:25]1[CH:30]=[C:29]([C:31]#[N:32])[CH:28]=[CH:27][C:26]=1[CH2:33][CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36].C([N:42](CC)CC)C>O1CCOCC1.CN(C=O)C.C(OCC)(=O)C>[C:31]([C:29]1[CH:28]=[CH:27][C:26]([CH2:33][CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])=[C:25]([O:24][CH2:23][CH2:22][NH:21][C:14]([CH:11]2[CH2:10][CH2:9][N:8]([C:6]3[CH:5]=[CH:4][N:3]=[C:2]([Cl:1])[N:42]=3)[CH2:13][CH2:12]2)=[O:16])[CH:30]=1)#[N:32]

Participants

Conditions

Temperature: 95 °C

Procedure

700 mg (2.60 mmol) of ethyl 1-(2-chloropyridine-4-yl)-4-piperidinecarboxylate was stirred in 5 ml of dioxane. 5 ml of 2 N hydrochloric acid was added to the obtained mixture, and they were stirred at 95° C. for 4 hours. The solvent was evaporated, and the obtained crude product was dissolved in 10 ml of DMF. 600 mg (2.16 mmol) of ethyl 3-[2-(2-aminoethoxy)-4-cyanophenyl]propionate hydrochloride, 548 mg (3.24 mmol) of 2-chloro-1,3-dimethylimidazonium chloride and 0.9 ml (6.48 mmol) of triethylamine were added to the obtained solution, and they were stirred overnight. After the treatment with ethyl acetate as the extraction solvent in an ordinary manner, the obtained crude product was purified by the silica gel column chromatography to obtain the title compound.

Workup

customThe solvent was evaporated
customthe obtained crude product
stirringwere stirred overnight
customwas purified by the silica gel column chromatography

Sources & evidence

ORD record: ord-a9a99cefa30548518f15b5477b493259
Source dataset: uspto-grants-2004_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06812231B2

Reaction notes

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