Water → Cycloheptane carboxylic acid [2-(4-cycloheptanecarbonyl-phenyl)-3H-imidazo[4,5-c]pyridine-6-yl]-amide

HRID 854089Notes

Reaction equation

HRID 854089 reaction equation
N[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:26][C:11]3[CH:12]=[N:13][C:14]([NH:16][C:17]([CH:19]4[CH2:25][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:27]1([C:34](Cl)=[O:35])[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1.O.C([O-])(O)=O.[Na+]>N1C=CC=CC=1>[CH:27]1([C:34]([C:2]2[CH:7]=[CH:6][C:5]([C:8]3[NH:26][C:11]4[CH:12]=[N:13][C:14]([NH:16][C:17]([CH:19]5[CH2:25][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:35])[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1

Participants

6

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 12556870Cycloheptanecarbonyl chlorideHCID 58932932Cycloheptane carboxylic acid [2-(4-amino-phenyl)-3H-imidazo[4,5-c]pyridine-6-yl]-amide

Product 1

HCID 86592844Cycloheptane carboxylic acid [2-(4-cycloheptanecarbonyl-phenyl)-3H-imidazo[4,5-c]pyridine-6-yl]-amideYield 40.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The amine 19 (0.094 g, 0.27 mmol) was taken in dry Pyridine (5 ml) and cycloheptane carbonyl chloride (0.100 ml, 0.622 mmol) was added and the solution stirred at room temperature overnight. Water was added followed by sat. NaHCO3 solution. The mixture was stirred at room temperature for 1 h. The solid was filtered, dried and passed through a SiO2 gel column, eluting with ethyl acetate afforded a white solid 20 (0.050 g, 39%). M.p. 194° C.; 1H NMR (DMSO-d6, 500 MHz): δ13.40 (1H, brs, NH), 10.09 (2H, s, NH), 8.81 (1H, brs), 8.145 (2H, d, J=9.0 MHz), 7.82 (2H, d, J=9.0 Hz), 2.74 (1H, m), 2.49 (1H, m), 1.91-1.25 (24H, m); EIMS m/z: 474.4 (M+1) and 472.6 (M−1); Anal (C28H35N5O2) C, H, N.

Workup

  1. stirringThe mixture was stirred at room temperature for 1 h
  2. filtrationThe solid was filtered
  3. customdried
  4. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-272cc49c70aa4716b736bd51ef656e57
Source dataset
uspto-grants-2007_08
Patent number
US07256287B2

Reaction notes

Loading…