4-Methylmorpholine → HCID 24738248, compound

HRID 19808Notes

Reaction equation

HRID 19808 reaction equation
[Cl:1][C:2]1[C:3]([F:15])=[C:4]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)[C:5]([OH:7])=O.[C:16]([C:20]1[CH:36]=[CH:35][C:23]([CH2:24][NH:25][CH2:26][CH2:27][C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=2)=[CH:22][CH:21]=1)([CH3:19])([CH3:18])[CH3:17].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN1CCOCC1>CN(C=O)C.[Cl-].[Na+].O.O>[C:16]([C:20]1[CH:36]=[CH:35][C:23]([CH2:24][N:25]([CH2:26][CH2:27][C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=2)[C:5](=[O:7])[C:4]2[CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=[C:2]([Cl:1])[C:3]=2[F:15])=[CH:22][CH:21]=1)([CH3:19])([CH3:17])[CH3:18]

Participants

8

Reactant 4

HCID 79724-MethylmorpholineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 27737513-Chloro-2-fluoro-5-(trifluoromethyl)benzoic acidHCID 29792506(4-Tert-butylbenzyl)-[2-(4-chlorophenyl)-ethyl]-amine

Product 1

HCID 24738248HCID 24738248, compoundYield 70.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 50 mg of 3-chloro-2-fluoro-5-trifluoromethyl-benzoic acid (0.206 mmol) and 68 mg (0.225 mmol) of (4-tert-butylbenzyl)-[2-(4-chlorophenyl)-ethyl]-amine in 3 ml of DMF were added 117 mg of HBTU (0.31 mmol) and 0.063 ml (0.62 mmol) of 4-methylmorpholine. After stirring the reaction mixture over night at RT it was poured on a mixture of 15 ml of brine and 15 ml of water and extracted with ethyl acetate. The combined organic phases were washed with brine, dried with magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography (silica gel; heptane/EtOAc 95:5) to give 76 mg (70%) of a light yellow amorphous material. MS (ISP) 526.0 (M+H)+. In analogy to example 1:

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic phases were washed with brine
  3. dry with materialdried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography (silica gel; heptane/EtOAc 95:5)

Sources & evidence

ORD record
ord-6882ab2e821742b9ba6189db1000c720
Source dataset
uspto-grants-2010_06
Patent number
US07745477B2

Reaction notes

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