2-Morpholinoethylamine → HCID 178523412, compound

HRID 77103Notes

Reaction equation

HRID 77103 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]([CH2:58][CH2:59][NH2:60])[CH2:54][CH2:53]1>>[N:55]1([CH2:58][CH2:59][NH:60][C:15]([C@@H:11]2[CH2:12][CH2:13][CH2:14][N:9]([C:6]3[CH:7]=[CH:8][C:3]([Cl:2])=[C:4]([C:18]4[NH:22][C:21]5[CH:23]=[CH:24][C:25]([F:27])=[CH:26][C:20]=5[N:19]=4)[CH:5]=3)[CH2:10]2)=[O:17])[CH2:56][CH2:57][O:52][CH2:53][CH2:54]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 178523412HCID 178523412, compoundYield 40%

Procedure

Method K—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 EtOAc to EtOAc:NH3 in MeOH (2M)/10:1) to obtain 0.05 g of the title compound (40%).

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 EtOAc to EtOAc:NH3 in MeOH (2M)/10:1)

Sources & evidence

ORD record
ord-19abd0d001c74be78e537654e02a69ca
Source dataset
uspto-grants-2014_09
Patent number
US08835648B2

Reaction notes

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