Cyclohexanecarbonyl chloride → Cyclohexanecarboxylic acid [2-(4-cyclohexanecarbonyl-phenyl)-3H-imidazo[4,5-c]pyridine-6-yl]-amide

HRID 854083Notes

Reaction equation

HRID 854083 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]([CH:19]4[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]4)=[O:18])=[CH:15][C:10]=3[N:9]=2)=[CH:4][CH:3]=1.[CH:26]1([C:32](Cl)=[O:33])[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1>C1COCC1.N1C=CC=CC=1>[CH:26]1([C:32]([C:2]2[CH:7]=[CH:6][C:5]([C:8]3[NH:25][C:11]4[CH:12]=[N:13][C:14]([NH:16][C:17]([CH:19]5[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]5)=[O:18])=[CH:15][C:10]=4[N:9]=3)=[CH:4][CH:3]=2)=[O:33])[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1

Participants

4

Reactant 2

HCID 75938Cyclohexanecarbonyl chlorideHCID 58932920Cyclohexanecarboxylic acid [2-(4-amino-phenyl)-3H-imidazo[4,5-c]pyridine-6-yl]-amide

Product 1

HCID 86592841Cyclohexanecarboxylic acid [2-(4-cyclohexanecarbonyl-phenyl)-3H-imidazo[4,5-c]pyridine-6-yl]-amideYield 53.2%

Reagents, catalysts & solvents 1

HCID 16069498Pyridine tetrahydrofuranSolvent

Procedure

To a stirring solution of 10 (0.080 g, 0.24 mmol) in dry THF/Pyridine (10 ml/0.300 ml) cyclohexane carbonyl chloride (0.060 ml, 0.38 mmol) was added and stirred at room temperature for 4 h. The reaction mixture was quenched with water and stirred for 30 min. The yellow solid was filtered, dried, and purified through a bed of SiO2 gel. Elution with ethyl acetate afforded the desired product 11 as light yellow solid 0.055 g (51%). Mp. 235° C.; 1HNMR (DMSO-d; 500 MHz): δ 12.99 (1H, brs, NH), 10.27 (1H, brs, NH), 10.07 (1H, brs, NH), 8.61 (1H, brs), 8.27 (1H, brs), 8.07 (2H, d, J=8.0 Hz), 7.79 (2H, d, J=9.0 Hz); 2.52 (1H, m), 2.36 (1H, m), 1.83-1.17 (20H, m); EIMS m/z: 446.5 (M+1) 444.6 (M−1); Anal. (C26H31N5O2.0.91H2O) C, H, N

Workup

  1. customThe reaction mixture was quenched with water
  2. stirringstirred for 30 min
  3. filtrationThe yellow solid was filtered
  4. customdried
  5. custompurified through a bed of SiO2 gel
  6. washElution with ethyl acetate

Sources & evidence

ORD record
ord-79dcda7552914dda95baf34b2f129372
Source dataset
uspto-grants-2007_08
Patent number
US07256287B2

Reaction notes

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