Hydrochloric Acid → HCID 22645192, compound

HRID 2187938Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:19])[C:7]=1[N:8]1[CH2:13][CH2:12][CH:11]([C:14]([O:16]CC)=O)[CH2:10][CH2:9]1.Cl.Cl.[NH2:22][CH2:23][CH2:24][O:25][C:26]1[CH:31]=[C:30]([C:32]#[N:33])[CH:29]=[CH:28][C:27]=1[CH2:34][CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37].C(N(CC)CC)C>O1CCOCC1.CN(C=O)C.C(OCC)(=O)C>[C:32]([C:30]1[CH:29]=[CH:28][C:27]([CH2:34][CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])=[C:26]([O:25][CH2:24][CH2:23][NH:22][C:14]([CH:11]2[CH2:10][CH2:9][N:8]([C:7]3[C:6]([Cl:19])=[CH:5][N:4]=[CH:3][C:2]=3[Cl:1])[CH2:13][CH2:12]2)=[O:16])[CH:31]=1)#[N:33]

Participants

Conditions

Temperature: 95 °C

Procedure

2.0 g (6.5 mmol) of ethyl 1-(3,5-dichloropyridine-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. 612 mg (2.27 mmol) of ethyl 3-[2-(2-aminoethoxy)-4-cyanophenyl]propionate hydrochloride, 575 mg (3.40 mmol) of 2-chloro-1,3-dimethylimidazonium chloride and 0.9 ml (6.8 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-ff2a2fa0f18e4c0089d21ca08860fd95
Source dataset: uspto-grants-2002_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06410538B2

Reaction notes

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