Morpholine → HCID 178491195, compound

HRID 1631445Notes

Reaction equation

HRID 1631445 reaction equation
Cl[CH2:2][C:3]([CH3:31])([CH3:30])[C:4]([N:6]([C@H:16]1[CH2:21][CH2:20][C@H:19]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:18][CH2:17]1)[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1)=[O:5].[C:32]([O-:35])([O-])=[O:33].[K+].[K+].[NH:38]1[CH2:43][CH2:42][O:41][CH2:40][CH2:39]1>CN(C=O)C>[N:38]1([C:32]([O:35][CH2:2][C:3]([CH3:31])([CH3:30])[C:4]([N:6]([C@H:16]2[CH2:21][CH2:20][C@H:19]([NH:22][C:23]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:29])[CH2:18][CH2:17]2)[CH2:7][C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)=[O:5])=[O:33])[CH2:43][CH2:42][O:41][CH2:40][CH2:39]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 178491192HCID 178491192, compound

Product 1

HCID 178491195HCID 178491195, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A stirred solution of 15B (75 mg, 0.166 mmol) in DMF (1 mL) was treated with K2CO3 (68.6 mg, 0.497 mmol), and morpholine (0.058 mL, 0.662 mmol). The reaction mixture was stirred at 90° C. overnight. The reaction mixture was concentrated and the residue was redissolved into small amount of MeOH, purified by preparative HPLC, (PHENOMENEX® Axia Luna 5 micron 30×100 mm, MeOH-water-TFA gradient). Concentration of the appropriate fractions provided 33 mg (37%) of 15C. MS (ES): m/z=548.2 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe residue was redissolved into small amount of MeOH
  3. custompurified by preparative HPLC, (PHENOMENEX® Axia Luna 5 micron 30×100 mm, MeOH-water-TFA gradient)

Sources & evidence

ORD record
ord-dec94dd754554743b9b7d80ea60c8826
Source dataset
uspto-grants-2014_07
Patent number
US08791257B2

Reaction notes

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