HCID 18405518, compound → HCID 70120561, compound

HRID 1018363Notes

Reaction equation

HRID 1018363 reaction equation
[C:1]12([CH2:11][CH2:12][C:13]3[NH:17][C:16]([CH:18]4[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]4)=[N:15][C:14]=3[C:24]([OH:26])=O)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[C:27]([O:31][C:32](=[O:46])[CH:33]([O:42][C:43](=[O:45])[CH3:44])[CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[C:37]([NH2:41])[CH:36]=1)([CH3:30])([CH3:29])[CH3:28]>>[C:27]([O:31][C:32](=[O:46])[CH:33]([O:42][C:43](=[O:45])[CH3:44])[CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[C:37]([NH:41][C:24]([C:14]2[N:15]=[C:16]([CH:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)[NH:17][C:13]=2[CH2:12][CH2:11][C:1]23[CH2:8][CH:7]4[CH2:9][CH:3]([CH2:4][CH:5]([CH2:6]4)[CH2:10]2)[CH2:2]3)=[O:26])[CH:36]=1)([CH3:30])([CH3:28])[CH3:29]

Participants

3

Reactant 2

HCID 18405518HCID 18405518, compoundHCID 57150058HCID 57150058, compound

Product 1

HCID 70120561HCID 70120561, compound

Procedure

5-(2-Adamantan-1-yl-ethyl)-2-cyclohexyl-1H-imidazole-4-carboxylic acid (Example 252) (690 mg, 1.94 mmol) was reacted with the product of step b (540 mg, 1.94 mmol) according to the procedure of Example 20, step d to afford colourless foam after purification by flash chromatography (silica, hexane/ethyl acetate 2:1) (287 mg, 24%). 1H NMR (300 MHz, CDCl3) 9.04 (1H, br s), 8.63 (1H, br s), 7.60 (2H, m), 7.25 (1H, m), 6.97 (1H, d), 5.11 (1H, m), 3.17-3.03 (4H, m), 2.80 (1H, m), 2.10-1.27 (399H, m).

Workup

  1. customto afford colourless foam
  2. customafter purification by flash chromatography (silica, hexane/ethyl acetate 2:1) (287 mg, 24%)

Sources & evidence

ORD record
ord-2fea8ef764534753be11db477577c3b5
Source dataset
uspto-grants-2002_11
Patent number
US06479531B1

Reaction notes

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