Hydrochloric Acid → (S)-2-(4-(Pyrrolidin-3-ylamino)quinolin-2-yl)phenol

HRID 2189205Notes

Reaction equation

HRID 2189205 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:17]=[C:16]([NH:18][C@H:19]2[CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20]2)[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1.Cl>CO.O1CCOCC1>[NH:21]1[CH2:22][CH2:23][C@H:19]([NH:18][C:16]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]=[C:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[OH:1])[CH:17]=2)[CH2:20]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 136068479(S)-tert-butyl 3-(2-(2-hydroxyphenyl)quinolin-4-ylamino)pyrrolidine-1-carboxylate

Product 1

HCID 136068438(S)-2-(4-(Pyrrolidin-3-ylamino)quinolin-2-yl)phenolYield 53.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

(S)-tert-butyl 3-(2-(2-hydroxyphenyl)quinolin-4-ylamino)pyrrolidine-1-carboxylate (0.050 g, 0.123 mmol) was dissolved in methanol (2 mL) and 4 M HCl in dioxane (5 mL) was added. After stirring for 12 hours, the solution was concentrated and purified by ion exchange chromatography on SCX-2 Isolute acidic resin (2 g), eluting with methanol and then 1 M ammonia in methanol. Further purification by preparative thin layer chromatography, eluting with 20% methanol in dichloromethane, gave the title compound as a solid (0.020 g, 53%).

Workup

  1. concentrationthe solution was concentrated
  2. custompurified by ion exchange chromatography on SCX-2 Isolute acidic resin (2 g)
  3. washeluting with methanol
  4. customFurther purification by preparative thin layer chromatography
  5. washeluting with 20% methanol in dichloromethane

Sources & evidence

ORD record
ord-5d355bf1f5c54bb6afda6c6373aa82d3
Source dataset
uspto-grants-2012_12
Patent number
US08324226B2

Reaction notes

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