Bicarbonate Ion → (2-(2-Amino-3-morpholinoquinolin-6-yl)-3-methylphenyl)(phenyl)methanol

HRID 1028949Notes

Reaction equation

HRID 1028949 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[C:25]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[O:26])[CH:8]=2)[N:3]=1.[BH4-].[Na+].C(=O)(O)[O-]>C(Cl)Cl.CO>[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:23]([CH3:24])=[CH:22][CH:21]=[CH:20][C:19]=3[CH:25]([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[OH:26])[CH:8]=2)[N:3]=1

Participants

6

Reactant 3

HCID 769Bicarbonate IonHCID 4311764Sodium borohydrideHCID 67325753(2-(2-Amino-3-morpholinoquinolin-6-yl)-3-methylphenyl)(phenyl)methanone

Product 1

HCID 67350995(2-(2-Amino-3-morpholinoquinolin-6-yl)-3-methylphenyl)(phenyl)methanol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

(2-(2-Amino-3-morpholinoquinolin-6-yl)-3-methylphenyl)(phenyl)methanone (0.152 g, 0.359 mmol) was dissolved in a mixture of DCM (4.0 mL) and MeOH (5.0 mL). Sodium borohydride (0.041 g, 1.077 mmol) was added to the mixture in three portions (each portion added at 3 h intervals) and the mixture was stirred at ambient temperature. The mixture was treated with DCM (10 mL) and saturated aqueous bicarbonate (10 mL) and stirred for 20 min. The phases were separated and the organic layer was concentrated to afford a yellow solid (2-(2-amino-3-morpholinoquinolin-6-yl)-3-methylphenyl)(phenyl)methanol which was used without further purification.

Workup

  1. additionadded at 3 h intervals) and the mixture
  2. stirringstirred for 20 min
  3. customThe phases were separated
  4. concentrationthe organic layer was concentrated

Sources & evidence

ORD record
ord-e75227d403fb40a8980ffc01956449d1
Source dataset
uspto-grants-2014_05
Patent number
US08735384B2

Reaction notes

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