Hydrochloric Acid → HCID 23144118, compound

HRID 337476Notes

Reaction equation

HRID 337476 reaction equation
[C:1]([C:6]1[S:10][C:9]([NH:11][C:12]([C:14]2[CH:19]=[CH:18][N:17]=[C:16]([CH2:20][Cl:21])[CH:15]=2)=[O:13])=[N:8][C:7]=1[C:22]1[O:23][CH:24]=[CH:25][CH:26]=1)(=[O:5])[CH2:2][CH2:3][CH3:4].[H-].[Na+].C(OCC)(=O)C.Cl.[CH3:36][N:37]([CH3:41])[CH2:38][CH2:39][OH:40]>>[ClH:21].[C:1]([C:6]1[S:10][C:9]([NH:11][C:12]([C:14]2[CH:19]=[CH:18][N:17]=[C:16]([CH2:20][O:40][CH2:39][CH2:38][N:37]([CH3:41])[CH3:36])[CH:15]=2)=[O:13])=[N:8][C:7]=1[C:22]1[O:23][CH:24]=[CH:25][CH:26]=1)(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 79022-(Dimethylamino)ethanolHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 23144626N-[5-Butyryl-4-(2-furyl)thiazol-2-yl]-2-(chloromethyl)pyridine-4-carboxamide

Product 1

HCID 23144118HCID 23144118, compoundYield 82%

Procedure

Compound 387 (247 mg, 0.635 mmol) was dissolved in 2-(dimethylamino)ethanol (3 mL), and 55% sodium hydride (55.0 mg, 1.27 mmol) was added thereto, followed by stirring at room temperature for 2 hours. The precipitated solid was collected by filtration to afford a free form of the entitled Compound. An ethyl acetate solution of 4 mol/L hydrogen chloride was added to the resulting free form, and the precipitated solid was collected by filtration to afford the entitled Compound 389 (248 mg, 82%).

Workup

  1. filtrationThe precipitated solid was collected by filtration
  2. customto afford a free form of the entitled Compound
  3. filtrationthe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-b19e9caa58494f42853d2d3509d122c9
Source dataset
uspto-grants-2014_11
Patent number
US08889718B2

Reaction notes

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