Potassium Carbonate → Pyridine-2-carboxylic acid [2-(4-adamantanecarbonyl-phenyl)-3H-imidazo[4,5-c]pyridin-6-yl]-amide

HRID 854093Notes

Reaction equation

HRID 854093 reaction equation
N[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:25][C:11]3[CH:12]=[N:13][C:14]([NH:16][C:17]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=4)=[O:18])=[CH:15][C:10]=3[N:9]=2)=[CH:4][CH:3]=1.[C:26]12([C:36](Cl)=[O:37])[CH2:35][CH:30]3[CH2:31][CH:32]([CH2:34][CH:28]([CH2:29]3)[CH2:27]1)[CH2:33]2.C([O-])([O-])=O.[K+].[K+]>N1C=CC=CC=1>[C:26]12([C:36]([C:2]3[CH:3]=[CH:4][C:5]([C:8]4[NH:25][C:11]5[CH:12]=[N:13][C:14]([NH:16][C:17]([C:19]6[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=6)=[O:18])=[CH:15][C:10]=5[N:9]=4)=[CH:6][CH:7]=3)=[O:37])[CH2:35][CH:30]3[CH2:31][CH:32]([CH2:34][CH:28]([CH2:29]3)[CH2:27]1)[CH2:33]2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 989151-Adamantanecarbonyl chlorideHCID 58932927Pyridine-2-carboxylic acid [2-(4-amino-phenyl)-3H-imidazo[4,5-c]pyridin-6-yl]-amide

Product 1

HCID 86592846Pyridine-2-carboxylic acid [2-(4-adamantanecarbonyl-phenyl)-3H-imidazo[4,5-c]pyridin-6-yl]-amideYield 41.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 22 (0.065 g, 0.197 mmol), adamantane carbonyl chloride (0.060 g, 0.30 mmol) in dry Pyridine (5 ml) was stirred at 80° C. for 2 h. After usual work-up the solid was treated with 10% K2CO3 for 1 h. The solid was filtered and passed through SiO2 gel, eluting with EtOAc affording diamide 24 (0.039 g, 40%). M.p. 305° C.; 1H NMR (DMSO-d6, 500 MHz): δ 13.19 (1H, brs, NH), 10.47 (1H, brs, NH), 9.39 (1H, brs), 8.765 (1H, d, J=4.5 Hz), 8.73 (1H, brs), 8.45 (1H, brs), 8.24 (1H, d, J=8.0 Hz), 8.14-8.09 (2H, m), 7.89 (2H, d, J=8.5 Hz), 7.72 (1H, dt, J=5.0 and 7.5 Hz), 2.0 (3H, brs), 1.92 (6H, brs), 1.72 (6H, brs); EIMS m/z: 493.5 (M+1); Anal (C29H28N6O2×1.23 H2O) C, H, N.

Workup

  1. filtrationThe solid was filtered
  2. washeluting with EtOAc

Sources & evidence

ORD record
ord-e388dfcf602848599964b7614329e8db
Source dataset
uspto-grants-2007_08
Patent number
US07256287B2

Reaction notes

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