Hydrochloric Acid → HCID 136030690, compound

HRID 2189197Notes

Reaction equation

HRID 2189197 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH2:11][C@@H:10]([NH:14][C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]=[C:17]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[OH:31])[N:16]=2)[CH2:9]1)=O)(C)(C)C.Cl>CO.O1CCOCC1>[NH:8]1[CH2:13][CH2:12][CH2:11][C@@H:10]([NH:14][C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]=[C:17]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[OH:31])[N:16]=2)[CH2:9]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 136068494HCID 136068494, compound

Product 1

HCID 136030690HCID 136030690, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

Crude (R)-3-[2-(2-hydroxy-phenyl)-quinazolin-4-yl-amino]-piperidine-1-carboxylic acid tert-butyl ester (˜1.0 mmol) was dissolved in methanol (4 mL) and 4M HCl in dioxane (10 mL) was added. After stirring for 24 hours the solution was concentrated and purified by ion exchange chromatography on SCX-2 Isolute acidic resin (5 g), eluting with methanol and then 1 M ammonia in methanol. Further purification by silica column chromatography, eluting with 20% methanol in dichloromethane, gave the title compound as a yellow solid (0.127 g, 40%).

Workup

  1. concentrationwas concentrated
  2. custompurified by ion exchange chromatography on SCX-2 Isolute acidic resin (5 g)
  3. washeluting with methanol
  4. customFurther purification by silica column chromatography
  5. washeluting with 20% methanol in dichloromethane

Sources & evidence

ORD record
ord-846541e3debf444b87dc0546448568d8
Source dataset
uspto-grants-2012_12
Patent number
US08324226B2

Reaction notes

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