Triethyloxonium tetrafluoroborate → [(S)-1-(3-Pyridin-2-yl-3H-imidazo[4,5-b]pyridin-2-yl)ethyl]carbamic acid tert-butyl ester

HRID 243052Notes

Reaction equation

HRID 243052 reaction equation
F[B-](F)(F)F.C([O+](CC)CC)C.[C:13]([O:17][C:18](=[O:25])[NH:19][C@H:20]([C:22](=O)[NH2:23])[CH3:21])([CH3:16])([CH3:15])[CH3:14].[N:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[NH:32][C:33]1[C:38](N)=[CH:37][CH:36]=[CH:35][N:34]=1>C1COCC1.C(O)C>[C:13]([O:17][C:18](=[O:25])[NH:19][C@H:20]([C:22]1[N:32]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=2)[C:27]2=[N:26][CH:31]=[CH:30][CH:29]=[C:28]2[N:23]=1)[CH3:21])([CH3:16])([CH3:15])[CH3:14]

Participants

6

Reactant 3

HCID 2723982Triethyloxonium tetrafluoroborateHCID 7015295Boc-Ala-NH2HCID 133823752-(2-Pyridylamino)-3-amino-pyridine

Product 1

HCID 68157645[(S)-1-(3-Pyridin-2-yl-3H-imidazo[4,5-b]pyridin-2-yl)ethyl]carbamic acid tert-butyl esterYield 98.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Triethyloxonium tetrafluoroborate (1.08 g, 5.66 mmol) was added to a solution of ((S)-1-carbamoylethyl)carbamic acid tert-butyl ester (1.00 g, 5.33 mmol) in THF (15 mL) at 20° C. under nitrogen and the resultant mixture stirred for 2 h then concentrated in vacuo. A solution of N2-pyridin-2-yl-pyridine-2,3-diamine (0.62 g, 3.33 mmol) in ethanol (15 mL) was added to the residue and the resultant solution stirred at 75° C. for 16 h. The reaction mixture was concentrated in vacuo and the residue partitioned between DCM (3×30 mL) and saturated aqueous NaHCO3 (30 mL). The combined DCM extracts were dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by chromatography (SiO2 0-5% (2M ammonia in methanol) in DCM) to give the title compound as an oil (1.11 g, 98%). LCMS (method H): Rt 2.73 min, [M+H]+ 340.

Workup

  1. concentrationthen concentrated in vacuo
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customthe residue partitioned between DCM (3×30 mL) and saturated aqueous NaHCO3 (30 mL)
  4. dry with materialThe combined DCM extracts were dried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified by chromatography (SiO2 0-5% (2M ammonia in methanol) in DCM)

Sources & evidence

ORD record
ord-03453920957f490a93d158d660a22eef
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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