Morpholine → [4-[6-Amino-5-(1-isopropyltriazol-4-yl)-3-pyridyl]-2-methoxy-phenyl]-morpholino-methanone

HRID 632491Notes

Reaction equation

HRID 632491 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:16]=[CH:15][C:11]([C:12](O)=[O:13])=[C:10]([O:17][CH3:18])[CH:9]=2)=[CH:4][C:3]=1[C:19]1[N:20]=[N:21][N:22]([CH:24]([CH3:26])[CH3:25])[CH:23]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH:51]1[CH2:56][CH2:55][O:54][CH2:53][CH2:52]1.CCN(C(C)C)C(C)C>CN(C=O)C>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:16]=[CH:15][C:11]([C:12]([N:51]3[CH2:56][CH2:55][O:54][CH2:53][CH2:52]3)=[O:13])=[C:10]([O:17][CH3:18])[CH:9]=2)=[CH:4][C:3]=1[C:19]1[N:20]=[N:21][N:22]([CH:24]([CH3:25])[CH3:26])[CH:23]=1

Participants

6

Reactant 4

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 902733904-(6-amino-5-(1-isopropyl-1H-1,2,3-triazol-4-yl)pyridin-3-yl)-2-methoxybenzoic acid

Product 1

HCID 77106365[4-[6-Amino-5-(1-isopropyltriazol-4-yl)-3-pyridyl]-2-methoxy-phenyl]-morpholino-methanoneYield 80.64%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(6-amino-5-(1-isopropyl-1H-1,2,3-triazol-4-yl)pyridin-3-yl)-2-methoxybenzoic acid (260 mg, 0.735 mmol) and HATU (418 mg, 1.10 mmol) in DMF (10.0 mL) were added morpholine (77 mg, 0.88 mmol) and DIPEA (0.4 mL, 2.205 mmol) at room temperature. The reaction mixture was stirred at room temperature for 18 h. The reaction mixture was poured into ice cold water, extracted with EtOAc (100 mL). The organic layer was washed with brine solution (50 mL), dried over anhydrous Na2SO4 and solvent was evaporated under reduced pressure. Crude compound was purified by column using 100-200 mesh silica gel. The column was eluted with 100% EtOAc to afford 250 mg (yield: 80.64%) of the title compound as pale yellow solid.

Workup

  1. additionThe reaction mixture was poured into ice cold water
  2. extractionextracted with EtOAc (100 mL)
  3. washThe organic layer was washed with brine solution (50 mL)
  4. dry with materialdried over anhydrous Na2SO4 and solvent
  5. customwas evaporated under reduced pressure
  6. customCrude compound was purified by column
  7. washThe column was eluted with 100% EtOAc

Sources & evidence

ORD record
ord-36e4b4f9d8564a59bf7dea2c6e0d4189
Source dataset
uspto-grants-2016_04
Patent number
US09321748B2

Reaction notes

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