Sodium borohydride → HCID 58529678, compound

HRID 1972744Notes

Reaction equation

HRID 1972744 reaction equation
[NH2:1][C:2]1[C:7]2=[CH:8][CH:9]=[C:10]([C:11]([CH:13]3[CH2:16][N:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:14]3)=[O:12])[N:6]2[N:5]=[CH:4][N:3]=1.[BH4-].[Na+]>CCO>[NH2:1][C:2]1[C:7]2=[CH:8][CH:9]=[C:10]([CH:11]([OH:12])[CH:13]3[CH2:16][N:15]([C:17]([O:19][C:20]([CH3:22])([CH3:21])[CH3:23])=[O:18])[CH2:14]3)[N:6]2[N:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 58529850HCID 58529850, compound

Product 1

HCID 58529678HCID 58529678, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
78 °C

Procedure

To a solution of tert-butyl 3-[(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)carbonyl]azetidine-1-carboxylate (1.35 g, 4.25 mmol) in EtOH (25 mL) was added sodium borohydride (644 mg, 17.01 mmol). The mixture was stirred at 78° C. for 2 h. The reaction was quenched with the addition of H2O (20 mL). The resulting solid was removed by filtration and the filtrate was extracted with EtOAc (3×20 mL). The combined organics were washed with brine, dried (Na2SO4), and concentrated to dryness to afford 1.0 g (74%) of the desired product. ES-MS m/z 320.16 [M+H]+, HPLC RT (min) 2.02.

Workup

  1. customThe reaction was quenched with the addition of H2O (20 mL)
  2. customThe resulting solid was removed by filtration
  3. extractionthe filtrate was extracted with EtOAc (3×20 mL)
  4. washThe combined organics were washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-25f3fe2affc748488aa730afb56239df
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

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