Acetic Acid → HCID 15870203, compound

HRID 369399Notes

Reaction equation

HRID 369399 reaction equation
C(O)(=O)C.[CH:5]([OH:7])=O.C(OC(=O)C)(=O)C.[Cl:15][C:16]1[CH:38]=[CH:37][C:19]([C:20]([C:22]2[N:26]([CH3:27])[C:25]([CH2:28][C:29]3[CH:34]=[CH:33][C:32]([NH2:35])=[CH:31][N:30]=3)=[CH:24][C:23]=2[CH3:36])=[O:21])=[CH:18][CH:17]=1>C1COCC1>[Cl:15][C:16]1[CH:17]=[CH:18][C:19]([C:20]([C:22]2[N:26]([CH3:27])[C:25]([CH2:28][C:29]3[CH:34]=[CH:33][C:32]([NH:35][CH:5]=[O:7])=[CH:31][N:30]=3)=[CH:24][C:23]=2[CH3:36])=[O:21])=[CH:37][CH:38]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 15870202{2-[5-(4-Chlorobenzoyl)-1,4-dimethyl-1H-pyrrol-2-ylmethyl]pyridin-5-yl}amine

Product 1

HCID 15870203HCID 15870203, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
55 °C

Procedure

The mixed anhydride of formic and acetic acid was prepared by adding formic acid (1 ml, 98%) dropwise to acetic anhydride (2 ml) and heating the mixture at 55° C. for 2.5 h. This reagent (2.2 ml) was then added to a solution of N-{2-[5-(4-chlorobenzoyl)-1,4-di-methyl-1H-pyrrol-2-ylmethyl]-pyridin-5-yl}amine (0.3 g, 0.88 mmol) in THF (7 ml), and the reaction mixture was heated overnight at 60° C. The solvents were removed in vacuo and the residue was crystallized from chloroform-hexane to give N-{2-[5-(4-chloro-benzoyl)-1,4-dimethyl-1H-pyrrol-2-ylmethyl]pyridin-5-yl}formamide (175 mg, 54%) as a solid, mp 166.6-167.7° C.

Workup

  1. temperaturethe reaction mixture was heated overnight at 60° C
  2. customThe solvents were removed in vacuo
  3. customthe residue was crystallized from chloroform-hexane

Sources & evidence

ORD record
ord-d9f2b9a3086a4ac68c88a8a2c3b21521
Source dataset
uspto-grants-2000_10
Patent number
US06136844

Reaction notes

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