1-Hydroxybenzotriazole → 1-(2-azidoethyl)-1H-benzimidazole-5-carboxylic acid (5-hydroxyadamantan-2-yl)-amide

HRID 555299Notes

Reaction equation

HRID 555299 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.[NH2:37][CH:38]1[CH:45]2[CH2:46][C:41]3([OH:48])[CH2:42][CH:43]([CH2:47][CH:39]1[CH2:40]3)[CH2:44]2.CCN=C=NCCCN(C)C.Cl>CN(C=O)C>[OH:48][C:41]12[CH2:46][CH:45]3[CH2:44][CH:43]([CH2:47][CH:39]([CH:38]3[NH:37][C:15]([C:13]3[CH:12]=[CH:11][C:10]4[N:6]([CH2:5][CH2:4][N:1]=[N+:2]=[N-:3])[CH:7]=[N:8][C:9]=4[CH:14]=3)=[O:17])[CH2:40]1)[CH2:42]2

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 28574474-Aminoadamantan-1-olHCID 866300581-(2-azidoethyl)-1H-benzimidazole-5-carboxylic acid

Product 1

HCID 866300631-(2-azidoethyl)-1H-benzimidazole-5-carboxylic acid (5-hydroxyadamantan-2-yl)-amideYield 93.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(2-azidoethyl)-1H-benzimidazole-5-carboxylic acid (0.65 g, 0.0028 mol) in dry DMF (5.0 mL) was added with stirring HOBt (0.46 g, 0.0034 mol), DIPEA (2.5 mL, 0.014 mol), 4-aminoadamantan-1-ol (0.685 g, 0.0034 mol) at 0° C. To the resulting mixture was added EDCl (0.65 g, 0.0034 mol) and stirred for 15 h at ambient temperature. The reaction mixture was diluted with ice water (100 mL) and extracted with EtOAc (3×50 mL) and the combined organic phases were washed with water, dried (Na2SO4) and the solvent evaporated affording (1.0 g, 93.5%) of 1-(2-azidoethyl)-1H-benzimidazole-5-carboxylic acid (5-hydroxyadamantan-2-yl)-amide. MS-ESI m/z 381 (M+1).

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-f40914f4f21d4e74aeb70fcb642deb87
Source dataset
uspto-grants-2011_11
Patent number
US08053431B2

Reaction notes

Loading…