Boron trifluoride etherate → 3-(1-Isopropyltriazol-4-yl)-5-[3-methoxy-4-(morpholinomethyl)phenyl]pyridin-2-amine

HRID 632492Notes

Reaction equation

HRID 632492 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([N:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)=O)=[C:10]([O:22][CH3:23])[CH:9]=2)=[CH:4][C:3]=1[C:24]1[N:25]=[N:26][N:27]([CH:29]([CH3:31])[CH3:30])[CH:28]=1.B(F)(F)F.CCOCC.[BH4-].[Na+]>C1COCC1>[CH:29]([N:27]1[CH:28]=[C:24]([C:3]2[C:2]([NH2:1])=[N:7][CH:6]=[C:5]([C:8]3[CH:13]=[CH:12][C:11]([CH2:14][N:16]4[CH2:17][CH2:18][O:19][CH2:20][CH2:21]4)=[C:10]([O:22][CH3:23])[CH:9]=3)[CH:4]=2)[N:25]=[N:26]1)([CH3:31])[CH3:30]

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 4311764Sodium borohydrideHCID 77106365[4-[6-Amino-5-(1-isopropyltriazol-4-yl)-3-pyridyl]-2-methoxy-phenyl]-morpholino-methanone

Product 1

HCID 760735713-(1-Isopropyltriazol-4-yl)-5-[3-methoxy-4-(morpholinomethyl)phenyl]pyridin-2-amineYield 51.81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of [4-[6-amino-5-(1-isopropyltriazol-4-yl)-3-pyridyl]-2-methoxy-phenyl]-morpholino-methanone (200 mg, 0.473 mmol) in THF (10.0 mL) was added BF3.Et2O (0.3 mL, 2.36 mmol) at 0° C. and stirred for 30 min. After 30 min, NaBH4 (89 mg, 2.36 mmol) was added at 0° C. and stirred at room temperature for 18 h. After cooling to 0° C., quenched with MeOH (2 mL) and heated to reflux for 6 h. The reaction mixture was diluted with EtOAc (50 mL), washed with water (30 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 100 mg (yield: 51.81%) of the title compound as white solid.

Workup

  1. waitAfter 30 min
  2. stirringstirred at room temperature for 18 h
  3. customquenched with MeOH (2 mL)
  4. temperatureheated
  5. temperatureto reflux for 6 h
  6. additionThe reaction mixture was diluted with EtOAc (50 mL)
  7. washwashed with water (30 mL)
  8. dry with materialdried over anhydrous Na2SO4 and solvent
  9. customwas evaporated under reduced pressure
  10. customCrude compound was purified by column
  11. washThe column was eluted with 100% EtOAc

Sources & evidence

ORD record
ord-aa82ffcb368f4820b5b0fd6b00a92610
Source dataset
uspto-grants-2016_04
Patent number
US09321748B2

Reaction notes

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