Acetyl chloride → N-[2-(4-Amino-furazan-3-yl)-1-ethyl-1H-imidazo[4,5-c]pyridin-7-ylmethyl]-N-piperidin-4-yl-acetamide

HRID 1394202

Reaction equation

HRID 1394202 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][CH2:15][C:16]2[C:17]3[N:24]([CH2:25][CH3:26])[C:23]([C:27]4[C:31]([NH2:32])=[N:30][O:29][N:28]=4)=[N:22][C:18]=3[CH:19]=[N:20][CH:21]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(=O)([O-])[O-].[K+].[K+].[C:39](Cl)(=[O:41])[CH3:40]>ClC1CC(C(C)C)CCC1(Cl)C>[NH2:32][C:31]1[C:27]([C:23]2[N:24]([CH2:25][CH3:26])[C:17]3[C:16]([CH2:15][N:14]([CH:11]4[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]4)[C:39](=[O:41])[CH3:40])=[CH:21][N:20]=[CH:19][C:18]=3[N:22]=2)=[N:28][O:29][N:30]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 11430Potassium CarbonateHCID 691594734-{[2-(4-Amino-furazan-3-yl)-1-ethyl-1H-imidazo[4,5-c]pyridin-7-ylmethyl]-amino}-piperidine-1-carboxylic Acid Tert-Butyl Ester

Product 1

HCID 59681782N-[2-(4-Amino-furazan-3-yl)-1-ethyl-1H-imidazo[4,5-c]pyridin-7-ylmethyl]-N-piperidin-4-yl-acetamideYield 59%

Reagents, catalysts & solvents 1

HCID 21946423DichloromenthaneSolvent

Procedure

The title compound from Example 191, Step 2 (145 mg, 0.3 mmol) in dichloromenthane at 0° C. was treated with potassium carbonate (90 mg, 0.66 mmol) followed by acetyl chloride (26 mg, 0.33 mL), and the mixture was stirred at room temperature for 1 hour. Purification of the residue by silica gel chromatography eluting with 10% methanol/dichloromethane afforded the title compound (68 mg, 10%). MS (ES+) m/e 484 [M+H]+.

Workup

  1. customPurification of the residue by silica gel chromatography
  2. washeluting with 10% methanol/dichloromethane

Sources & evidence

ORD record
ord-88090faa2f0d4f05ac9f784c1cb1c44f
Source dataset
uspto-grants-2008_03
Patent number
US07348339B2

Linked notes

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