Tetrahydrofuran → 1H-Benzoimidazole-2-carboxylic acid (8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl)-amide

HRID 1784957Notes

Reaction equation

HRID 1784957 reaction equation
Cl[C:2](Cl)(Cl)[C:3]1[NH:7][C:6]2[CH:8]=[CH:9][CH:10]=[CH:11][C:5]=2[N:4]=1.Cl.Cl.[CH3:16][N:17]1[CH:22]2[CH2:23][CH2:24][CH:18]1[CH2:19][CH:20]([NH2:25])[CH2:21]2.[O:26]1CCCC1>>[CH3:16][N:17]1[CH:22]2[CH2:23][CH2:24][CH:18]1[CH2:19][CH:20]([NH:25][C:2]([C:3]1[NH:7][C:6]3[CH:8]=[CH:9][CH:10]=[CH:11][C:5]=3[N:4]=1)=[O:26])[CH2:21]2

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 77133Benzimidazole, 2-trichloromethyl-HCID 27759288-methyl-8-azabicyclo[3.2.1]octan-3-amine Dihydrochloride

Product 1

HCID 103791501H-Benzoimidazole-2-carboxylic acid (8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl)-amideYield 10%

Procedure

The reaction was carried out as described in General Procedure 2 using 2-trichloromethyl-1H-benzoimidazole (Example 1, 100 mg, 0.42 mmol) and 8-methyl-8-azabicyclo[3.2.1]oct-3-ylamine dihydrochloride (172 mg, 0.84 mmol) in tetrahydrofuran (THF, 3 mL). Purification afforded 10 mg (10%) of the title compound. MS (ESI): mass calculated for C16H20N4O, 284.16; m/z found, 285.2 [M+H]+. 1H NMR (400 MHz, CDCl3): 11.70 (br s, 1H), 8.10 (d, J=8.0 Hz, 1H), 7.76 (br s, 1H), 7.43 (br s, 1H), 7.35-7.33 (m, 2H), 4.37 (q, J=7.1 Hz, 1H), 3.25-3.23 (m, 2H), 2.49 (s, 3H), 2.39-2.33 (m, 2H), 2.23 (s, 3H), 2.23-2.18 (m, 2H), 2.02-1.96 (m, 2H), 1.97 (d, J=14.4 Hz, 2H).

Workup

  1. customPurification

Sources & evidence

ORD record
ord-f6608355280f42a3bd26ad96883a3177
Source dataset
uspto-grants-2009_03
Patent number
US07504426B2

Reaction notes

Loading…