Morpholine → HCID 178463300, compound

HRID 1469160Notes

Reaction equation

HRID 1469160 reaction equation
Br[CH2:2][C:3]#[C:4][C:5]1[CH:6]=[C:7]([N:16]([C@H:19]2[CH2:24][CH2:23][C@H:22]([N:25]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH3:26])[CH2:21][CH2:20]2)[CH2:17][CH3:18])[C:8]([CH3:15])=[C:9]([CH:14]=1)[C:10]([O:12][CH3:13])=[O:11].[NH:34]1[CH2:39][CH2:38][O:37][CH2:36][CH2:35]1>CN(C=O)C>[C:30]([O:29][C:27]([N:25]([CH3:26])[C@H:22]1[CH2:21][CH2:20][C@H:19]([N:16]([CH2:17][CH3:18])[C:7]2[C:8]([CH3:15])=[C:9]([CH:14]=[C:5]([C:4]#[C:3][CH2:2][N:34]3[CH2:39][CH2:38][O:37][CH2:36][CH2:35]3)[CH:6]=2)[C:10]([O:12][CH3:13])=[O:11])[CH2:24][CH2:23]1)=[O:28])([CH3:33])([CH3:32])[CH3:31]

Participants

4

Reactant 2

HCID 8083MorpholineHCID 178463279HCID 178463279, compound

Product 1

HCID 178463300HCID 178463300, compoundYield 98.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of methyl 5-(3-bromoprop-1-yn-1-yl)-3-(((trans)-4-((tert-butoxy carbonyl)-(methyl)amino)cyclohexyl)(ethyl)amino)-2-methylbenzoate (1 equiv.) in DMF, morpholine (5 equiv.) was added and reaction was stirred for 12 h at room temperature. On completion, the reaction was quenched with ice water and extracted with dichloromethane. The combined organic layers were washed with water, dried, concentrated under reduced pressure to afford desired crude title compound that was used in the next step without further purification (98.7% yield)

Workup

  1. customreaction
  2. customOn completion, the reaction was quenched with ice water
  3. extractionextracted with dichloromethane
  4. washThe combined organic layers were washed with water
  5. customdried
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e9a853f4c2d24d259f6534b851b86ce3
Source dataset
uspto-grants-2015_04
Patent number
US09006242B2

Reaction notes

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