Morpholine → HCID 23729222, compound

HRID 1911774Notes

Reaction equation

HRID 1911774 reaction equation
[F:1][C:2]([F:44])([F:43])[C:3]1[CH:4]=[C:5]([CH:36]=[C:37]([C:39]([F:42])([F:41])[F:40])[CH:38]=1)[CH2:6][N:7]([CH2:15][C:16]1[C:17]([N:27]([CH2:32][CH:33]2[CH2:35][CH2:34]2)[CH2:28][CH:29]2[CH2:31][CH2:30]2)=[N:18][C:19]2[C:24]([CH:25]=1)=[CH:23][CH:22]=[CH:21][C:20]=2[CH3:26])[C:8]1[N:13]=[CH:12][C:11](Br)=[CH:10][N:9]=1.CC(C)([O-])C.[Na+].[NH:51]1[CH2:56][CH2:55][O:54][CH2:53][CH2:52]1>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[F:1][C:2]([F:44])([F:43])[C:3]1[CH:4]=[C:5]([CH:36]=[C:37]([C:39]([F:42])([F:41])[F:40])[CH:38]=1)[CH2:6][N:7]([CH2:15][C:16]1[C:17]([N:27]([CH2:32][CH:33]2[CH2:35][CH2:34]2)[CH2:28][CH:29]2[CH2:31][CH2:30]2)=[N:18][C:19]2[C:24]([CH:25]=1)=[CH:23][CH:22]=[CH:21][C:20]=2[CH3:26])[C:8]1[N:13]=[CH:12][C:11]([N:51]2[CH2:56][CH2:55][O:54][CH2:53][CH2:52]2)=[CH:10][N:9]=1

Participants

6

Reactant 3

HCID 8083MorpholineHCID 23676156Sodium t-butoxideHCID 23729206HCID 23729206, compound

Product 1

HCID 23729222HCID 23729222, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

A mixture of (3-{[(3,5-bis-trifluoromethyl-benzyl)-(5-bromo-pyrimidin-2-yl)-amino]-methyl}-8-methyl-quinolin-2-yl)-bis-cyclopropylmethyl-amine (0.32 g,0.47 mmol), tris(dibenzylideneacetone)dipalladium (0.07 g, 0.08 mmol), (2-biphenyl)-di-tert-butylphosphine (0.02 g, 0.06 mmol), sodium tert-butoxide (0.09 g, 1 mmol), morpholine (0.08 ml, 0.9 mmol) in toluene was stirred at ambient temperature for 24 h. Thereafter, the reaction mixture is quenched with water and extracted with ethyl acetate (2×30 mL). The combined organic extracts was washed with brine, dried over sodium sulfate and concentrated in vacuo. The crude mixture was purified by chromatography using silica gel to afford the title compound as a colorless solid (0.11 g, 35%).

Workup

  1. customThereafter, the reaction mixture is quenched with water
  2. extractionextracted with ethyl acetate (2×30 mL)
  3. washThe combined organic extracts was washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe crude mixture was purified by chromatography

Sources & evidence

ORD record
ord-9cd8c3bd7b424fa3bc15a4ee559416fc
Source dataset
uspto-grants-2013_12
Patent number
US08604055B2

Reaction notes

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