Methanol → HCID 77106562, compound

HRID 632499Notes

Reaction equation

HRID 632499 reaction equation
B(F)(F)F.CCOCC.[NH2:10][C:11]1[N:16]=[CH:15][C:14]([C:17]2[CH:18]=[C:19]([C:24]([N:26]3[CH2:31][CH2:30][O:29][CH2:28][CH2:27]3)=O)[CH:20]=[C:21]([Cl:23])[CH:22]=2)=[CH:13][C:12]=1[C:32]1[N:33]=[N:34][N:35]([CH:37]([CH3:39])[CH3:38])[CH:36]=1.[BH4-].[Na+].CO>C1COCC1.O>[Cl:23][C:21]1[CH:22]=[C:17]([C:14]2[CH:13]=[C:12]([C:32]3[N:33]=[N:34][N:35]([CH:37]([CH3:39])[CH3:38])[CH:36]=3)[C:11]([NH2:10])=[N:16][CH:15]=2)[CH:18]=[C:19]([CH2:24][N:26]2[CH2:27][CH2:28][O:29][CH2:30][CH2:31]2)[CH:20]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 8000Boron trifluoride etherateHCID 4311764Sodium borohydrideHCID 77106561HCID 77106561, compound

Product 1

HCID 77106562HCID 77106562, compoundYield 20.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

BF3.Et2O in THF (47-49%) (0.70 mL, 2.34 mmol) was added to a solution of [3-[6-amino-5-(1-isopropyltriazol-4-yl)-3-pyridyl]-5-chloro-phenyl]-morpholino-methanone (200 mg, 0.46 mmol) in THF (10.0 mL) at 0° C., then reaction mixture was stirred for 30 min, added NaBH4 (89 mg, 2.36 mmol) at 0° C., reaction mixture was slowly warmed to RT, stirred for 16 h. Reaction mixture was cooled to 0° C., added MeOH (5.0 mL) to the reaction mixture, heated to 70° C. for 2 h. The reaction mixture was diluted with water (50 mL) and extracted with ethyl acetate (2×30 mL). Combined organic layers was dried over Na2SO4 and concentrated under reduced pressure. Crude product was purified by silica (100-200 mesh) column eluted with 2% MeOH in DCM to afford 39 mg (Yield: 20.2%) of the title compound. This was converted to its HCl salt by using HCl in ether (2M) to afford 45 mg as a pale gray solid.

Workup

  1. customreaction mixture
  2. customreaction mixture
  3. stirringstirred for 16 h
  4. customReaction mixture
  5. temperaturewas cooled to 0° C.
  6. temperatureheated to 70° C. for 2 h
  7. extractionextracted with ethyl acetate (2×30 mL)
  8. dry with materialCombined organic layers was dried over Na2SO4
  9. concentrationconcentrated under reduced pressure
  10. customCrude product was purified by silica (100-200 mesh) column
  11. washeluted with 2% MeOH in DCM

Sources & evidence

ORD record
ord-9fc698c57a914614b2b25dbba103f7d1
Source dataset
uspto-grants-2016_04
Patent number
US09321748B2

Reaction notes

Loading…