Formaldehyde → HCID 25065975, compound

HRID 2196607Notes

Reaction equation

HRID 2196607 reaction equation
C=O.CO.[NH:5]1[CH2:8][CH:7]([O:9][C:10]2[CH:15]=[CH:14][C:13]([S:16][C:17]3[C:18]([C:30]([NH:32][C:33]4[S:37][N:36]=[C:35]([CH3:38])[N:34]=4)=[O:31])=[N:19][C:20]([S:23][C:24]4[N:28]([CH3:29])[CH:27]=[N:26][N:25]=4)=[CH:21][CH:22]=3)=[CH:12][CH:11]=2)[CH2:6]1.[C:39](=O)([O-])O.[Na+]>[Cl-].[Zn+2].[Cl-].[B-]C#N.[Na+].CO.O>[CH3:39][N:5]1[CH2:6][CH:7]([O:9][C:10]2[CH:15]=[CH:14][C:13]([S:16][C:17]3[C:18]([C:30]([NH:32][C:33]4[S:37][N:36]=[C:35]([CH3:38])[N:34]=4)=[O:31])=[N:19][C:20]([S:23][C:24]4[N:28]([CH3:29])[CH:27]=[N:26][N:25]=4)=[CH:21][CH:22]=3)=[CH:12][CH:11]=2)[CH2:8]1

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 887MethanolHCID 516892Sodium BicarbonateHCID 69050567HCID 69050567, compound

Product 1

HCID 25065975HCID 25065975, compound

Reagents, catalysts & solvents 2

HCID 131730118HCID 131730118, compoundCatalystHCID 962WaterSolvent

Procedure

0.20 ml of aqueous 37% formaldehyde solution and 0.10 ml of 0.3 M zinc chloride-sodium cyanotrihydroborate/methanol solution (J. Org. Chem. 1985, 50, 1927-1932) were added to a methanol (0.40 ml) solution of 13 mg of 3-{[4-(azetidin-3-yloxy)phenyl]thio}-N-(3-methyl-1,2,4-thiadiazol-5-yl)-6-[(4-methyl-4H-1,2,4-triazol-3-yl)thio]pyridine-2-carboxamide obtained in the step 2, and stirred at room temperature for 30 minutes. Aqueous saturated sodium hydrogencarbonate solution and saturated saline water were added to it, and extracted with chloroform. The organic layer was dried with anhydrous magnesium sulfate, the solvent was evaporated away under reduced pressure, and the residue was purified through partitioning thin-layer chromatography (NH-PLC05 (by Fuji Silicia Chemical), chloroform/methanol=95/5) to obtain 12 mg of the entitled compound as a yellow solid.

Workup

  1. customobtained in the step 2
  2. extractionextracted with chloroform
  3. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
  4. customthe solvent was evaporated away under reduced pressure
  5. customthe residue was purified
  6. customthrough partitioning thin-layer chromatography (NH-PLC05 (by Fuji Silicia Chemical), chloroform/methanol=95/5)

Sources & evidence

ORD record
ord-f95fdf516ed34f6ba1e711a8f96ba530
Source dataset
uspto-grants-2012_12
Patent number
US08338460B2

Reaction notes

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