Methanol → HCID 86623780, compound

HRID 1426870Notes

Reaction equation

HRID 1426870 reaction equation
[Cl:1][C:2]1[S:6][C:5]([O:7][C:8]2[C:13]([CH3:14])=[CH:12][C:11]([N:15]=[CH:16][N:17]([CH2:19][CH3:20])[CH3:18])=[C:10]([CH3:21])[CH:9]=2)=[N:4][C:3]=1[CH:22]=O.Cl.[NH2:25][O:26][C:27]([CH3:30])([CH3:29])[CH3:28].CO>O>[C:27]([O:26][N:25]=[CH:22][C:3]1[N:4]=[C:5]([O:7][C:8]2[C:13]([CH3:14])=[CH:12][C:11]([N:15]=[CH:16][N:17]([CH2:19][CH3:20])[CH3:18])=[C:10]([CH3:21])[CH:9]=2)[S:6][C:2]=1[Cl:1])([CH3:30])([CH3:29])[CH3:28]

Participants

5

Reactant 3

HCID 887MethanolHCID 2777906O-tert-butylhydroxylamine hydrochlorideHCID 59823515HCID 59823515, compound

Product 1

HCID 86623780HCID 86623780, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 0.23 g (0.50 mmol) of N′-{4-[(5-chloro-4-formyl-1,3-thiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylimidoformamide and 63 mg (0.50 mmol) of 2-(aminooxy)-2-methylpropane hydrochloride in a solvent mixture of 10 ml of methanol and 3 ml of water was stirred at ambient temperature for 5 days. Evaporation of the solvents and column chromatography of the crude mixture (gradient cyclohexane->ethyl acetate) yielded 130 mg (0.37 mmol) 61% of N′-[4-({4-[(tert-butoxyimino)methyl]-5-chloro-1,3-thiazol-2-yl}oxy)-2,5-dimethylphenyl]-N-ethyl-N-methylimidoformamide. Log P (pH 2.3)=2.65

Workup

  1. customEvaporation of the solvents and column chromatography of the crude mixture (gradient cyclohexane->ethyl acetate)

Sources & evidence

ORD record
ord-34e7970316a440a895f61273d505dd16
Source dataset
uspto-grants-2015_01
Patent number
US08933107B2

Reaction notes

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