1,1'-Carbonyldiimidazole → HCID 58728636, compound

HRID 1992064Notes

Reaction equation

HRID 1992064 reaction equation
[C:1]([C:3]1([C:6]([OH:8])=O)[CH2:5][CH2:4]1)#[N:2].C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:21][C:22]1[N:26]([CH:27]2[CH2:33][C@H:32]3[N:34]([CH2:35][CH2:36][C:37]4([C:43]5[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=5)[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]4)[C@H:29]([CH2:30][CH2:31]3)[CH2:28]2)[C:25]2[CH:49]=[CH:50][CH:51]=[CH:52][C:24]=2[N:23]=1>ClCCCl>[CH3:21][C:22]1[N:26]([CH:27]2[CH2:33][C@H:32]3[N:34]([CH2:35][CH2:36][C:37]4([C:43]5[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=5)[CH2:38][CH2:39][N:40]([C:6]([C:3]5([C:1]#[N:2])[CH2:5][CH2:4]5)=[O:8])[CH2:41][CH2:42]4)[C@H:29]([CH2:30][CH2:31]3)[CH2:28]2)[C:25]2[CH:49]=[CH:50][CH:51]=[CH:52][C:24]=2[N:23]=1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 27332591-Cyanocyclopropanecarboxylic acidHCID 10322237HCID 10322237, compound

Product 1

HCID 58728636HCID 58728636, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 1-cyanocyclopropane-carboxylic acid (38.9 mg, 0.351 mmole) in 1 ml of DCE was added carbonyldiimidazole (38.0 mg, 0.234 mmole) and the mixture was stirred until gas evolution stopped. 2-Methyl-1-{(1R,5S)-8-[2-(4-phenyl-4-piperidinyl)ethyl]-8-azabicyclo[3.2.1]oct-3-yl}-1H-benzimidazole (50.0 mg, 0.117 mmole) was added and the resulting mixture was stirred overnight. The solvent was evaporated and the reaction mixture was flashed on silica using a gradient of 1-8% MeOH in CHCl3 to afford 1-[(4-{2-[(1R,5S)-3-(2-methyl-1H-benzimidazol-1-yl)-8-azabicyclo[3.2.1]oct-8-yl]ethyl}-4-phenyl-1-piperidinyl)carbonyl]cyclopropanecarbonitrile. MS ES+ 522 (M+H). 1H NMR (300 MHz, chloroform-d) δ ppm 1.6 (m, J=43.1 Hz, 6H), 1.9 (d, J=25.3 Hz, 10H), 2.4 (m, J=10.0 Hz, 4H), 2.6 (s, 3H), 3.3 (m, 3H), 3.5 (m, 1H), 4.1 (m, 2H), 4.7 (m, 1H), 7.3 (m, 8H), 7.7 (m, 1H).

Workup

  1. stirringthe resulting mixture was stirred overnight
  2. customThe solvent was evaporated

Sources & evidence

ORD record
ord-16ea33e65ad643c28fc2b790e885001b
Source dataset
uspto-grants-2010_01
Patent number
US07645771B2

Reaction notes

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