(2-(2-Amino-3-morpholinoquinolin-6-yl)-3-methylphenyl)(pyrazin-2-yl)methanol → 6-(2-Methyl-6-(pyrazin-2-ylmethyl)phenyl)-3-morpholinoquinolin-2-amine

HRID 1029012Notes

Reaction equation

HRID 1029012 reaction equation
[NH2:1][C:2]1[C:11]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:18]3[C:23]([CH3:24])=[CH:22][CH:21]=[CH:20][C:19]=3[CH:25]([C:27]3[CH:32]=[N:31][CH:30]=[CH:29][N:28]=3)O)[CH:8]=2)[N:3]=1>CC(O)C.Cl>[CH3:24][C:23]1[CH:22]=[CH:21][CH:20]=[C:19]([CH2:25][C:27]2[CH:32]=[N:31][CH:30]=[CH:29][N:28]=2)[C:18]=1[C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[N:3]=[C:2]([NH2:1])[C:11]([N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1)=[CH:10]2

Participants

4

Reactant 1

HCID 53329361(2-(2-Amino-3-morpholinoquinolin-6-yl)-3-methylphenyl)(pyrazin-2-yl)methanol

Product 1

HCID 533295356-(2-Methyl-6-(pyrazin-2-ylmethyl)phenyl)-3-morpholinoquinolin-2-amine

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 3776IsopropanolSolvent

Procedure

A solution of (2-(2-amino-3-morpholinoquinolin-6-yl)-3-methylphenyl)(pyrazin-2-yl)methanol (0.040 g, 0.094 mmol, prepared as Example 36 above) in i-PrOH and 5N HCl (15 mL) was refluxed for 15 h, or until starting material was consumed. The mixture was brought to RT, carefully washed with 5N NaOH and extracted with DCM. The combined organics were dried over Na2SO4, filtered, concentrated and purified by HPLC to afford a light brown solid as 6-(2-methyl-6-(pyrazin-2-ylmethyl)phenyl)-3-morpholinoquinolin-2-amine. MS (ESI, pos. ion) m/z: 412 (M+1).

Workup

  1. customwas consumed
  2. customwas brought to RT
  3. washcarefully washed with 5N NaOH
  4. extractionextracted with DCM
  5. dry with materialThe combined organics were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by HPLC

Sources & evidence

ORD record
ord-dadd8309185f473997c5711979b742ed
Source dataset
uspto-grants-2014_05
Patent number
US08735384B2

Reaction notes

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