1-Adamantanecarbonyl chloride → Adamantane carboxylic acid [2-(4-nitro-phenyl)-3H-imidazo[4,5-c]pyridine-6-yl]-amide

HRID 854085

Reaction equation

HRID 854085 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[NH:19][C:13]3[CH:14]=[N:15][C:16]([NH2:18])=[CH:17][C:12]=3[N:11]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:20]12([C:30](Cl)=[O:31])[CH2:29][CH:24]3[CH2:25][CH:26]([CH2:28][CH:22]([CH2:23]3)[CH2:21]1)[CH2:27]2>C1COCC1.N1C=CC=CC=1>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[NH:19][C:13]3[CH:14]=[N:15][C:16]([NH:18][C:30]([C:20]45[CH2:29][CH:24]6[CH2:23][CH:22]([CH2:28][CH:26]([CH2:25]6)[CH2:27]4)[CH2:21]5)=[O:31])=[CH:17][C:12]=3[N:11]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 989151-Adamantanecarbonyl chlorideHCID 589329182-(4-Nitro-phenyl)-3H-imidazo[4,5-c]pyridine-6-ylamine

Product 1

HCID 58932930Adamantane carboxylic acid [2-(4-nitro-phenyl)-3H-imidazo[4,5-c]pyridine-6-yl]-amideYield 67.5%

Reagents, catalysts & solvents 1

HCID 16069498Pyridine tetrahydrofuranSolvent

Procedure

To a stirring solution of nitro amine 8 (0.240 g, 0.94 mmol) in dry THF-Pyridine (15 ml/0.400 ml), adamantane carbonyl chloride (0.280 g, 1.41 mmol) was added and the mixture stirred at room temperature for 3 h. The reaction was quenched by addition of water and the resulting yellow solid was filtered and passed through a SiO2 gel using EtOAc as a eluent to give 13 (0.265 g, 67%). 1H NMR (DMSO-d6, 500 MHz): δ 13.51 (1H, brs, NH), 9.60 (1H, brs, NH), 8.78 (1H, s), 8.45-8.40 (4H, m), 8.32 (1H, s), 2.00-1.60 (15H, m); EIMS m/z: 418.5 (M+1) and 416 (M−1).

Workup

  1. customThe reaction was quenched by addition of water
  2. filtrationthe resulting yellow solid was filtered

Sources & evidence

ORD record
ord-df9a2dcfad254f8f884c67b16ee2122d
Source dataset
uspto-grants-2007_08
Patent number
US07256287B2

Linked notes

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