Hydrochloric Acid → HCID 178487141, compound

HRID 1749979Notes

Reaction equation

HRID 1749979 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[C:11]2\[O:12][C:13]3[C:20]([C:21]#[C:22][CH2:23][CH:24]4[CH2:29][CH2:28][N:27](C(OC(C)(C)C)=O)[CH2:26][CH2:25]4)=[C:19]([O:37][CH3:38])[CH:18]=[CH:17][C:14]=3[C:15]\2=[O:16])=[N:2]1.Cl>C(Cl)Cl.O1CCOCC1>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[C:11]2\[O:12][C:13]3[C:20]([C:21]#[C:22][CH2:23][CH:24]4[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]4)=[C:19]([O:37][CH3:38])[CH:18]=[CH:17][C:14]=3[C:15]\2=[O:16])=[N:2]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 178487145HCID 178487145, compound

Product 1

HCID 178487141HCID 178487141, compoundYield 52.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of tert-butyl (Z)-4-(3-{2-[(1H-indazol-3-yl)methylene]-6-methoxy-3-oxo-2,3-dihydrobenzofuran-7-yl}prop-2-ynyl)piperidine-1-carboxylate (0.0293 g, 0.0570 mmol) in methylene chloride (2 mL) was added with a 4 M solution of hydrogen chloride in 1,4-dioxane (2 mL), and the mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated, the resulting residue was added with saturated aqueous sodium hydrogencarbonate, and the precipitated solid was collected by filtration. The solid was washed with water, and then dried under reduced pressure to obtain (Z)-2-[(1H-indazol-3-yl)methylene]-6-methoxy-7-[3-(piperidin-4-yl)prop-1-ynyl]benzofuran-3(2H)-one (0.0123 g, 52%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionthe resulting residue was added with saturated aqueous sodium hydrogencarbonate
  3. filtrationthe precipitated solid was collected by filtration
  4. washThe solid was washed with water
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-7e6e35b2a7aa4a95ab84746a5a0a416f
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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