4-Methylmorpholine → HCID 66791505, compound

HRID 1096630Notes

Reaction equation

HRID 1096630 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([NH:9][CH2:10][CH2:11][CH2:12][O:13][CH3:14])[C:6]([NH2:15])=[CH:5][CH:4]=1.[C:16]([N:23]1[CH2:31][CH2:30][CH2:29][C@@H:25]([C:26](O)=[O:27])[CH2:24]1)([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17].CN1CCOCC1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([NH:15][C:26]([C@@H:25]2[CH2:29][CH2:30][CH2:31][N:23]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:24]2)=[O:27])=[C:7]([NH:9][CH2:10][CH2:11][CH2:12][O:13][CH3:14])[CH:8]=1

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 6435161-(1,1-Dimethylethyl) (3R)-1,3-piperidinedicarboxylateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66791978HCID 66791978, compound

Product 1

HCID 66791505HCID 66791505, compoundYield 155.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

5-Methoxy-N1-(3-methoxypropyl)benzene-1,2-diamine (42B) (1.81 mmol, 380 mg) in DMF (20 mL) was added (R)-(−)-N-Boc-nipecotic acid (2.35 mmol, 541 mg) and N-methylmorpholine (5.43 mmol, 0.60 mL). The reaction mixture was stirred at rt for 5 min and then added HATU (2.72 mmol, 1.03 g) and kept stirring at rt overnight. The reaction mixture was poured into H2O, extracted with EtOAc. The extract was washed with H2O, NaHCO3, brine, dried over MgSO4 and filtered. The filtrate was concentrated in vacuo and purified by flash chromatography (silica gel, EtOAc-hexane: 1:2) to afford (R)-tert-butyl 3-(4-methoxy-2-(3-methoxypropylamino)phenylcarbarnoyl)piperidine-1-carboxylate (42C) (2.82 mmol, 1.19 g, three-step yield: 80.6%). ESI-MS: m/z 422.5 (M+H)+.

Workup

  1. extractionextracted with EtOAc
  2. washThe extract was washed with H2O, NaHCO3, brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo
  6. custompurified by flash chromatography (silica gel, EtOAc-hexane: 1:2)

Sources & evidence

ORD record
ord-22d9f964df2349c9b955f4ce325be205
Source dataset
uspto-grants-2012_03
Patent number
US08138168B1

Reaction notes

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