Hydrochloric Acid → HCID 66705934, compound

HRID 2276374Notes

Reaction equation

HRID 2276374 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH:10]([C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20]([NH:22][C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][N:24]=3)=[O:21])=[CH:15][CH:14]=2)[CH2:9]1)=O)(C)(C)C.Cl>C1COCC1.O1CCOCC1>[ClH:29].[Cl:29][C:26]1[CH:27]=[CH:28][C:23]([NH:22][C:20]([NH:19][C:16]2[CH:17]=[CH:18][C:13]([CH:10]3[CH2:11][CH2:12][NH:8][CH2:9]3)=[CH:14][CH:15]=2)=[O:21])=[N:24][CH:25]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 66705878HCID 66705878, compound

Product 1

HCID 66705934HCID 66705934, compoundYield 187.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of (RS)-3-{4-[3-(5-chloro-pyridin-2-yl)-ureido]-phenyl}-pyrrolidine-1-carboxylic acid tert-butyl ester (210 mg) in THF (4 ml) was added dropwise a solution of hydrogen chloride in dioxane (1.89 ml, 4 M solution) and the mixture was heated at 60° C. overnight. The mixture was then cooled to 0° C. and the ensuing crystals were collected by filtration, washing with ethyl acetate, and were dried in vacuo at 60° C. to afford (RS)-1-(5-chloro-pyridin-2-yl)-3-(4-pyrrolidin-3-yl-phenyl)-urea hydrochloride (167 mg, 94%) as a beige crystalline solid. MS (ISP): 319.1 ([{37Cl}M+H]+), 317.2 ([{35Cl}M+H]+).

Workup

  1. temperatureThe mixture was then cooled to 0° C.
  2. filtrationthe ensuing crystals were collected by filtration
  3. washwashing with ethyl acetate
  4. customwere dried in vacuo at 60° C.

Sources & evidence

ORD record
ord-dc40a6939f794d76974881d2a9aafd3a
Source dataset
uspto-grants-2015_09
Patent number
US09132136B2

Reaction notes

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