Hydrochloric Acid → HCID 135921449, compound

HRID 2189217Notes

Reaction equation

HRID 2189217 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N: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]=[C:13]([C:31]#[C:32][CH2:33][OH:34])[CH:14]=2)[N:9]=1.Cl>CO.O1CCOCC1>[OH:34][CH2:33][C:32]#[C:31][C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[OH:1])[N:17]=[C:16]2[NH:18][C@H:19]1[CH2:23][CH2:22][NH:21][CH2:20]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 136068452HCID 136068452, compound

Product 1

HCID 135921449HCID 135921449, compoundYield 27.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

(S)-tert-Butyl 3-(2-(2-hydroxyphenyl)-6-(3-hydroxyprop-1-ynyl)quinazolin-4-ylamino)pyrrolidine-1-carboxylate (0.028 g, 0.061 mmol) was dissolved in methanol (1 mL) and 4 M HCl in dioxane (2 mL) added. After stirring for 12 hours, the solution was concentrated and purified by ion exchange chromatography on SCX-2 (solute 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 yellow solid (0.006 g, 27%).

Workup

  1. concentrationthe solution was concentrated
  2. custompurified by ion exchange chromatography on SCX-2 (solute 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-4abadcae56be4652a9eae498b0236c70
Source dataset
uspto-grants-2012_12
Patent number
US08324226B2

Reaction notes

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