1-Hydroxybenzotriazole → [1-(2-azidoethyl)-1H-benzimidazol-5-yl]-(octahydroquinolin-1-yl)methanone

HRID 555297Notes

Reaction equation

HRID 555297 reaction equation
[N:1]([CH2:4][CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][C:13]([C:15]([OH:17])=O)=[CH:14][C:9]=2[N:8]=[CH:7]1)=[N+:2]=[N-:3].C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[NH:37]1[CH:46]2[CH:41]([CH2:42][CH2:43][CH2:44][CH2:45]2)[CH2:40][CH2:39][CH2:38]1.CCN=C=NCCCN(C)C.Cl>CN(C=O)C>[N:1]([CH2:4][CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][C:13]([C:15]([N:37]3[CH:46]4[CH:41]([CH2:42][CH2:43][CH2:44][CH2:45]4)[CH2:40][CH2:39][CH2:38]3)=[O:17])=[CH:14][C:9]=2[N:8]=[CH:7]1)=[N+:2]=[N-:3]

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 92911DecahydroquinolineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 866300581-(2-azidoethyl)-1H-benzimidazole-5-carboxylic acid

Product 1

HCID 86630061[1-(2-azidoethyl)-1H-benzimidazol-5-yl]-(octahydroquinolin-1-yl)methanoneYield 98.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(2-azidoethyl)-1H-benzimidazole-5-carboxylic acid (1 g, 0.00433 mol) in dry DMF (7.0 mL) was added with stirring HOBt (0.876 g, 0.00649 mol), DIPEA (2.25 mL, 0.0129 mol), decahydroquinoline (0.902 g, 0.00649 mol) at 0° C. To the resulting mixture was added EDCl (1.24 g, 0.00649 mol) and stirred for 15 h at an ambient temperature. The reaction mixture was diluted with ice water (100 mL) and extracted with EtOAc (3×50 mL). The combined organic phases were washed with water, dried (Na2SO4) and the solvent evaporated to give [1-(2-azidoethyl)-1H-benzimidazol-5-yl]-(octahydroquinolin-1-yl)methanone (1.5 g, 98%).

Workup

  1. extractionextracted with EtOAc (3×50 mL)
  2. washThe combined organic phases were washed with water
  3. dry with materialdried (Na2SO4)
  4. customthe solvent evaporated

Sources & evidence

ORD record
ord-9b74c64754f34a08936a5501c2d14352
Source dataset
uspto-grants-2011_11
Patent number
US08053431B2

Reaction notes

Loading…