N,O-Dimethylhydroxylamine → N-methoxy-N-methylthiazole-4-carboxamide

HRID 1778306Notes

Reaction equation

HRID 1778306 reaction equation
[S:1]1[CH:5]=[C:4]([C:6]([OH:8])=O)[N:3]=[CH:2]1.[CH3:9][NH:10][O:11][CH3:12].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(Cl)Cl.O>[CH3:12][O:11][N:10]([CH3:9])[C:6]([C:4]1[N:3]=[CH:2][S:1][CH:5]=1)=[O:8]

Participants

6

Reactant 3

HCID 14232N,O-DimethylhydroxylamineHCID 3042714-Thiazolecarboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 16203794N-methoxy-N-methylthiazole-4-carboxamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of thiazole-4-carboxylic acid (1 g, 7.74 mmol), N,O-dimethylhydroxylamine (1.51 g, 15.5 mmol), and HATU (3.83 g, 10.07 mmol) in CH2Cl2 (25 mL) was added TEA (4.84 mL, 34.85 mmol). The reaction was stirred at room temperature overnight. The reaction was diluted with CH2Cl2 and water. The organics were concentrated and purified by chromatography (60-70% EtOAc/hexanes) to yield N-methoxy-N-methylthiazole-4-carboxamide as a clear oil. 1H NMR (CDCl3) δ: 8.83 (s, 1H), 8.10 (s, 1H), 3.79 (s, 3H), 3.46 (s, 3H)

Workup

  1. concentrationThe organics were concentrated
  2. custompurified by chromatography (60-70% EtOAc/hexanes)

Sources & evidence

ORD record
ord-636d70edacf8493cabf42e903c78e1be
Source dataset
uspto-grants-2016_02
Patent number
US09266835B2

Reaction notes

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