2-Aminothiazole → HCID 59408784, compound

HRID 1188127Notes

Reaction equation

HRID 1188127 reaction equation
[CH3:1][N:2]([CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][O:11]1)[C:3]1[S:4][C:5]([CH:8]=O)=[CH:6][N:7]=1.[NH2:16][C:17]1[S:18][CH:19]=[CH:20][N:21]=1.[BH4-].[Na+]>C1(C)C=CC=CC=1.CCO>[CH3:1][N:2]([CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][O:11]1)[C:3]1[S:4][C:5]([CH2:8][NH:16][C:17]2[S:18][CH:19]=[CH:20][N:21]=2)=[CH:6][N:7]=1

Participants

6

Reactant 3

HCID 21552-AminothiazoleHCID 4311764Sodium borohydrideHCID 59408736HCID 59408736, compound

Product 1

HCID 59408784HCID 59408784, compoundYield 17%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

A solution of 2-(methyl(tetrahydro-2H-pyran-2-yl)amino)thiazole-5-carbaldehyde (250 mg, 1.10 mmol) and 2-aminothiazole (110 mg, 1.10 mmol) in toluene (11 mL) and molecular sieves 3 Å were stirred at reflux overnight. The strongly yellow solution of the corresponding imine was then poured over NaBH4 (212 mg, 5.61 mmol) in hot EtOH (80 mL). The colorless solution was filtered, concentrated and purified by column chromatography yielding N-methyl-N-(tetrahydro-2H-pyran-2-yl)-5-((thiazol-2-ylamino)methyl)thiazol-2-amine (50 mg, 17%) as a solid.

Workup

  1. temperatureat reflux overnight
  2. filtrationThe colorless solution was filtered
  3. concentrationconcentrated
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-50a0e5ad13404172a0fc839a301c4695
Source dataset
uspto-grants-2014_03
Patent number
US08673940B2

Reaction notes

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