5-(azidomethyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazole → (1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazol-5-yl)methanamine

HRID 475175Notes

Reaction equation

HRID 475175 reaction equation
[N:1]([CH2:4][C:5]1[CH:19]=[CH:18][C:8]2[N:9]([CH:12]3[CH2:17][CH2:16][CH2:15][CH2:14][O:13]3)[CH:10]=[N:11][C:7]=2[CH:6]=1)=[N+]=[N-]>CO.[Pd]>[O:13]1[CH2:14][CH2:15][CH2:16][CH2:17][CH:12]1[N:9]1[C:8]2[CH:18]=[CH:19][C:5]([CH2:4][NH2:1])=[CH:6][C:7]=2[N:11]=[CH:10]1

Participants

4

Reactant 1

HCID 712722435-(azidomethyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazole

Product 1

HCID 46739877(1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazol-5-yl)methanamineYield 82%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 26 (1.0 g, 3.9 mmol) in MeOH (20 mL) was added 20% Pd—C (200 mg), and the mixture was stirred vigorously under H2 (1 atm.) atmosphere at RT for 18 h. The reaction mixture was filtered through a pad of Celite® and concentrated in vacuo to afford 740 mg (82%) (1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazol-5-yl)methanamine (28) as yellow oil, which was used into the next step without further purification: MS (ESI) m/z=232.2 [M+1]+.

Workup

  1. filtrationThe reaction mixture was filtered through a pad of Celite®
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-df10de474b5a42d69930dab4cf9504c7
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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