Acetic Acid → HCID 9847660, compound

HRID 2299294Notes

Reaction equation

HRID 2299294 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:13]([N:15]1[CH:20]=[C:19]([C:21]([OH:23])=O)[C:18](=[O:24])[C:17]2[CH:25]=[C:26]([I:28])[S:27][C:16]1=2)[CH3:14].[Cl:29][C:30]1[CH:37]=[CH:36][C:33]([CH2:34][NH2:35])=[CH:32][CH:31]=1.CC(O)=O>CN(C=O)C>[Cl:29][C:30]1[CH:37]=[CH:36][C:33]([CH2:34][NH:35][C:21]([C:19]2[C:18](=[O:24])[C:17]3[CH:25]=[C:26]([I:28])[S:27][C:16]=3[N:15]([CH2:13][CH3:14])[CH:20]=2)=[O:23])=[CH:32][CH:31]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 660364-ChlorobenzylamineHCID 682631,1'-CarbonyldiimidazoleHCID 132177217-Ethyl-2-iodo-4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carboxylic acid

Product 1

HCID 9847660HCID 9847660, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Carbonyldiimidazole (0.290 g) is added to a solution of 7-ethyl-2-iodo-4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carboxylic acid (Eur. J. Med. Chem. 1987, 22, 139) (0.520 g) in DMF (13 mL). The reaction is heated to 60° C. and stirred for 18 h. The reaction mixture is cooled to rt, and 4-chlorobenzylamine (0.22 mL) is added. The reaction is stirred at rt for 7 h. The reaction mixture is poured into 20% aqueous HOAc (50 mL), and the resulting off-white solid is filtered off. This material is recrystallized twice from methanol to yield 0.372 g (53%) of the title compound as an off-white, crystalline solid.

Workup

  1. temperatureThe reaction mixture is cooled to rt
  2. stirringThe reaction is stirred at rt for 7 h
  3. filtrationthe resulting off-white solid is filtered off
  4. customThis material is recrystallized twice from methanol

Sources & evidence

ORD record
ord-3f5ef00f8e564d65af414003bbeae265
Source dataset
uspto-grants-2002_12
Patent number
US06495683B2

Reaction notes

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