Hydrochloric Acid → (2-(2-Amino-3-morpholinoquinolin-6-yl)-3-methylphenyl)(phenyl)methanone

HRID 1028960Notes

Reaction equation

HRID 1028960 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:25]([CH3:26])=[CH:24][CH:23]=[CH:22][C:19]=3[C:20]#N)[CH:8]=2)[N:3]=1.[C:27]1([Mg]Cl)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C1C[O:38]CC1.Cl>>[NH2:1][C:2]1[C:11]([N:12]2[CH2:13][CH2:14][O:15][CH2:16][CH2:17]2)=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:18]3[C:25]([CH3:26])=[CH:24][CH:23]=[CH:22][C:19]=3[C:20]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[O:38])[CH:8]=2)[N:3]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 673450552-(2-Amino-3-morpholinoquinolin-6-yl)-3-methylbenzonitrileHCID 178478979HCID 178478979, compound

Product 1

HCID 67325753(2-(2-Amino-3-morpholinoquinolin-6-yl)-3-methylphenyl)(phenyl)methanone

Conditions

Temperature
60 °C

Procedure

To a sealed tube containing 2-(2-amino-3-morpholinoquinolin-6-yl)-3-methylbenzonitrile (0.20 g, 0.581 mmol, prepared as in Example 14, Step 1) was added phenylmagnesium chloride, 2.0M solution in THF (1.16 mL, 2.323 mmol) under N2 atmosphere. The mixture was heated at 60° C. overnight and the conversion was completed, determined by LCMS. The mixture was allowed to cool to RT and treated with aqueous 2N HCl (1 ml) carefully. The resulted mixture was heated at 60° C. for 7 h until the imine was consumed. The product mixture was concentrated and then diluted with MeOH and purified on HPLC (10-100% MeCN/H2O with 0.1% TFA modifier) to afford (2-(2-amino-3-morpholinoquinolin-6-yl)-3-methylphenyl)(phenyl)methanone (TFA salt).

Workup

  1. temperatureto cool to RT
  2. customwas consumed
  3. concentrationThe product mixture was concentrated
  4. additiondiluted with MeOH
  5. custompurified on HPLC (10-100% MeCN/H2O with 0.1% TFA modifier)

Sources & evidence

ORD record
ord-0adf08fc6cc848be92085b21eb001de5
Source dataset
uspto-grants-2014_05
Patent number
US08735384B2

Reaction notes

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