2-Morpholinoethylamine → HCID 178521026, compound

HRID 77104Notes

Reaction equation

HRID 77104 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][CH2:12][C@@H:11]([C:15]([OH:17])=O)[CH2:10]2)=[CH:5][C:4]=1[C:18]1[NH:22][C:21]2[CH:23]=[CH:24][C:25]([F:27])=[CH:26][C:20]=2[N:19]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[O:52]1[CH2:57][CH2:56][N:55](CCN)[CH2:54][CH2:53]1>>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][CH2:12][C@@H:11]([C:15]([N:55]3[CH2:56][CH2:57][O:52][CH2:53][CH2:54]3)=[O:17])[CH2:10]2)=[CH:5][C:4]=1[C:18]1[NH:22][C:21]2[CH:23]=[CH:24][C:25]([F:27])=[CH:26][C:20]=2[N:19]=1

Participants

4

Reactant 3

HCID 4082852-MorpholinoethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178479763HCID 178479763, compound

Product 1

HCID 178521026HCID 178521026, compoundYield 29%

Procedure

Method L—Step a To a mixture of (R)-1-[4-Chloro-3-(5-fluoro-1H-benzoimidazol-2-yl)-phenyl]-piperidine-3-carboxylic acid hydrochloride (obtained as described in general method 3,4, step e) (0.01 g, 0.27 mmol) in dcm (2 mL), HATU (0.10 g, 0.28 mmol), TEA (0.08 mL, 0.56 mmol) and 2-morpholinoethylamine (0.04 g, 0.33 mmol) were added. The reaction mixture was stirred at room temperature overnight, washed with ammonium chloride solution (2 mL), filtered through a phase separator and organic solvent was removed. The crude was then purified by SCX column and flash chromatography (eluent: gradient from cyclohexane:EtOAc/1:1 to 0:1 to EtOAc:NH3 in MeOH (2M)/10:1). A further purification by preparative HPLC was done to obtain 0.03 g of the title compound (29%).

Workup

  1. additionwere added
  2. washwashed with ammonium chloride solution (2 mL)
  3. filtrationfiltered through a phase separator and organic solvent
  4. customwas removed
  5. customThe crude was then purified by SCX column and flash chromatography (eluent: gradient from cyclohexane:EtOAc/1:1 to 0:1 to EtOAc:NH3 in MeOH (2M)/10:1)
  6. customA further purification by preparative HPLC

Sources & evidence

ORD record
ord-54d3cf63ad7b492e98b81a5d7511568b
Source dataset
uspto-grants-2014_09
Patent number
US08835648B2

Reaction notes

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