2-Morpholinoethylamine → HCID 178423452, compound

HRID 77107Notes

Reaction equation

HRID 77107 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](O)=[O:16])[CH2:10]2)=[CH:5][C:4]=1[C:18]1[NH:22][C:21]2[CH:23]=[CH:24][C:25]([CH3:27])=[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.[N:52]1([CH2:58][CH2:59][NH2:60])[CH2:57][CH2:56][O:55][CH2:54][CH2:53]1.C([O-])(O)=O.[Na+]>ClCCl>[N:52]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]([CH3:27])=[CH:26][C:20]=5[N:19]=4)[CH:5]=3)[CH2:10]2)=[O:16])[CH2:57][CH2:56][O:55][CH2:54][CH2:53]1

Participants

6

Reactant 4

HCID 4082852-MorpholinoethylamineHCID 516892Sodium BicarbonateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178423453HCID 178423453, compound

Product 1

HCID 178423452HCID 178423452, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
35 °C

Procedure

Method O—Step a To a vial with (R)-1-[4-Chloro-3-(5-methyl-1H-benzoimidazol-2-yl)-phenyl]-piperidine-3-carboxylic acid hydrochloride (obtained as described in general method 3,4, step e) (0.10 g, 0.25 mmol), HATU (0.10 g, 0.26 mmol), TEA (0.07 mL, 0.53 mmol) and 2-morpholin-4-yl-ethylamine (0.04 mL, 0.33 mmol), dichloromethane (2 mL) was added and the reaction mixture was heated at 35° C. overnight. Reaction was cooled to room temperature, saturated NaHCO3 solution (2 mL) was added with stirring, the organic layer recovered by filtration through phase separator, and the solvent removed under reduced pressure. The crude was purified by SCX and flash chromatography (eluent; gradient cyclohexane:ethylacetate from 100:0 to 3:1) to obtain 0.05 g of the title compound (42%).

Workup

  1. customReaction
  2. temperaturewas cooled to room temperature
  3. filtrationthe organic layer recovered by filtration through phase separator
  4. customthe solvent removed under reduced pressure
  5. customThe crude was purified by SCX and flash chromatography (eluent; gradient cyclohexane:ethylacetate from 100:0 to 3:1)

Sources & evidence

ORD record
ord-af7c18cd2ecc4c149d4263f8e573ea0e
Source dataset
uspto-grants-2014_09
Patent number
US08835648B2

Reaction notes

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