Hydrochloric Acid → HCID 66705928, compound

HRID 2276376Notes

Reaction equation

HRID 2276376 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]([C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][N:23]=3)=[O:21])=[CH:15][CH:14]=2)[CH2:9]1)=O)(C)(C)C.Cl>C1COCC1.O1CCOCC1>[ClH:28].[NH:8]1[CH2:12][CH2:11][CH:10]([C:13]2[CH:14]=[CH:15][C:16]([NH:19][C:20]([C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][N:23]=3)=[O:21])=[CH:17][CH:18]=2)[CH2:9]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 66705936HCID 66705936, compound

Product 1

HCID 66705928HCID 66705928, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of (RS)-3-{4-[(5-chloro-pyridine-2-carbonyl)-amino]-phenyl}-pyrrolidine-1-carboxylic acid tert-butyl ester (310 mg) in THF (6 ml) was added dropwise a solution of hydrogen chloride in dioxane (2.9 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 diethyl ether, and were dried in vacuo at 60° C. to afford (RS)-5-chloro-pyridine-2-carboxylic acid (4-pyrrolidin-3-yl-phenyl)-amide hydrochloride as a light yellow solid. MS (ISP): 304.2 ([{37Cl}M+H]+), 302.3 ([{35Cl}M+H]+).

Workup

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

Sources & evidence

ORD record
ord-5170dd3f277846ddafde3d16ba04737f
Source dataset
uspto-grants-2015_09
Patent number
US09132136B2

Reaction notes

Loading…