HCID 57912454, compound → 3-[2,6-Dimethoxy-4-(methoxymethyl)phenyl]-6-methoxypyrazolo[5,1-b][1,3]thiazole-7-amine

HRID 1971782Notes

Reaction equation

HRID 1971782 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:21]=[C:20]([O:22][CH3:23])[C:19]([N:24]=O)=[C:16]2[S:17][CH:18]=1>[C].[Pd].C(OCC)(=O)C>[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:21]=[C:20]([O:22][CH3:23])[C:19]([NH2:24])=[C:16]2[S:17][CH:18]=1

Participants

4

Reactant 1

HCID 57912454HCID 57912454, compound

Product 1

HCID 579124433-[2,6-Dimethoxy-4-(methoxymethyl)phenyl]-6-methoxypyrazolo[5,1-b][1,3]thiazole-7-amineYield 63.5%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Ethyl acetate (109 mL) and 10% palladium-carbon powder (50% wet: 2.34 g, 2.2 mmol) were added in that order to 3-[2,6-dimethoxy-4-(methoxymethyl)phenyl]-6-methoxy-7-nitrosopyrazolo[5,1-b][1,3]thiazole (2.34 g, 6.44 mmol), and the mixture was stirred for 1 hour under a hydrogen atmosphere. The mixture was filtered with Celite and the solvent in the obtained filtrate was distilled off under reduced pressure. The residue was purified by (NH)silica gel column chromatography (ethyl acetate) to obtain the title compound (1.43 g, 4.09 mmol).

Workup

  1. filtrationThe mixture was filtered with Celite
  2. distillationthe solvent in the obtained filtrate was distilled off under reduced pressure
  3. customThe residue was purified by (NH)silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-3c91d05d861e474490c8609c92888aba
Source dataset
uspto-grants-2013_04
Patent number
US08431603B2

Reaction notes

Loading…