Sodium Carbonate → 3-[2,6-Dimethoxy-4-(methoxymethyl)phenyl]-6-methyl-2-(methylsulfinyl)-N,N-dipropylpyrazolo[5,1-b][1,3]thiazole-7-amine

HRID 41272Notes

Reaction equation

HRID 41272 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH2:9][O:10][CH3:11])[CH:6]=[C:5]([O:12][CH3:13])[C:4]=1[C:14]1[N:15]2[N:23]=[C:22]([CH3:24])[C:21]([N:25]([CH2:29][CH2:30][CH3:31])[CH2:26][CH2:27][CH3:28])=[C:16]2[S:17][C:18]=1[S:19][CH3:20].ClC1C=CC=C(C(OO)=[O:40])C=1.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[CH3:13][O:12][C:5]1[CH:6]=[C:7]([CH2:9][O:10][CH3:11])[CH:8]=[C:3]([O:2][CH3:1])[C:4]=1[C:14]1[N:15]2[N:23]=[C:22]([CH3:24])[C:21]([N:25]([CH2:29][CH2:30][CH3:31])[CH2:26][CH2:27][CH3:28])=[C:16]2[S:17][C:18]=1[S:19]([CH3:20])=[O:40]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 58223475HCID 58223475, compound

Product 1

HCID 670950473-[2,6-Dimethoxy-4-(methoxymethyl)phenyl]-6-methyl-2-(methylsulfinyl)-N,N-dipropylpyrazolo[5,1-b][1,3]thiazole-7-amineYield 22.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a dichloromethane (670 μl) solution of 3-[2,6-dimethoxy-4-(methoxymethyl)phenyl]-6-methyl-2-(methylthio)-N,N-dipropylpyrazolo[5,1-b][1,3]thiazole-7-amine (31.5 mg, 0.068 mmol) was added 3-chloroperbenzoic acid (23.4 mg, 0.136 mmol), and the mixture was stirred at room temperature for 10 minutes. To the reaction mixture, a saturated aqueous solution of sodium carbonate was added, the mixture was extracted with dichloromethane, and then, the organic layer was dried over anhydrous magnesium sulfate. The mixture was filtered to yield a filtrate, and the solvent in the filtrate was distilled off under reduced pressure. The residue was purified by thin-layer silica gel chromatography (chloroform:methanol=12:1) to obtain 7.3 mg (0.0152 mmol) of the title compound.

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationThe mixture was filtered
  4. customto yield a filtrate
  5. distillationthe solvent in the filtrate was distilled off under reduced pressure
  6. customThe residue was purified by thin-layer silica gel chromatography (chloroform:methanol=12:1)

Sources & evidence

ORD record
ord-5d5f2517da2b4d2bbc73a2aaaa2d8484
Source dataset
uspto-grants-2013_09
Patent number
US08530504B2

Reaction notes

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