2,2-Dimethyl-4-(6-morpholino-5-nitropyridin-3-yl)morpholine → 5-(2,2-Dimethylmorpholino)-2-morpholinopyridin-3-amine

HRID 1431385Notes

Reaction equation

HRID 1431385 reaction equation
[CH3:1][C:2]1([CH3:23])[O:7][CH2:6][CH2:5][N:4]([C:8]2[CH:9]=[N:10][C:11]([N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)=[C:12]([N+:14]([O-])=O)[CH:13]=2)[CH2:3]1>CO.[Pd]>[CH3:1][C:2]1([CH3:23])[CH2:3][N:4]([C:8]2[CH:13]=[C:12]([NH2:14])[C:11]([N:17]3[CH2:18][CH2:19][O:20][CH2:21][CH2:22]3)=[N:10][CH:9]=2)[CH2:5][CH2:6][O:7]1

Participants

4

Reactant 1

HCID 596311902,2-Dimethyl-4-(6-morpholino-5-nitropyridin-3-yl)morpholine

Product 1

HCID 596312285-(2,2-Dimethylmorpholino)-2-morpholinopyridin-3-amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 2,2-dimethyl-4-(6-morpholino-5-nitropyridin-3-yl)morpholine (490 mg, 1.52 mmol; described herein) in 30 mL MeOH was reduced in a Thalles H-Cube® hydrogenator using a 10% Pd/C CatCart column (20 bar, 25° C., 1 mL/min flow rate.) The reaction mixture was then concentrated, diluted with EtOAc, and extracted with 1M HCl. The aq. layer was washed with DCM and basified with 1M NaOH. The product was extracted with EtOAc, dried (magnesium sulfate), and concentrated, affording 5-(2,2-dimethylmorpholino)-2-morpholinopyridin-3-amine as a beige powder. Mass Spectrum (ESI) m/e=293.2 (M+1).

Workup

  1. concentrationwas then concentrated
  2. additiondiluted with EtOAc
  3. extractionextracted with 1M HCl
  4. washThe aq. layer was washed with DCM and basified with 1M NaOH
  5. extractionThe product was extracted with EtOAc
  6. dry with materialdried (magnesium sulfate)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-d35c25082341449ca19ac65fe62a9fb8
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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