O-Methylhydroxylamine hydrochloride → 1-ethyl-3-[7-[(E)-N-methoxy-C-methylcarbonimidoyl]-5-phenylmethoxy-1,3-benzothiazol-2-yl]urea

HRID 712288Notes

Reaction equation

HRID 712288 reaction equation
Cl.[CH3:2][O:3][NH2:4].[C:5]([C:8]1[C:16]2[S:15][C:14]([NH:17][C:18]([NH:20][CH2:21][CH3:22])=[O:19])=[N:13][C:12]=2[CH:11]=[C:10]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:9]=1)(=O)[CH3:6]>CN(C=O)C>[CH2:24]([O:23][C:10]1[CH:9]=[C:8](/[C:5](/[CH3:6])=[N:4]/[O:3][CH3:2])[C:16]2[S:15][C:14]([NH:17][C:18]([NH:20][CH2:21][CH3:22])=[O:19])=[N:13][C:12]=2[CH:11]=1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

4

Reactant 2

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 866640001-(7-Acetyl-5-benzyloxy-1,3-benzothiazol-2-yl)-3-ethyl-urea

Product 1

HCID 872225491-ethyl-3-[7-[(E)-N-methoxy-C-methylcarbonimidoyl]-5-phenylmethoxy-1,3-benzothiazol-2-yl]ureaYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

O-Methyl hydroxylamine hydrochloride (289 mg, 3.46 mmol) was added to 1-(7-acetyl-5-benzyloxy-1,3-benzothiazol-2-yl)-3-ethyl-urea (650 mg, 1.73 mmol) in DMF (7 mL). The reaction mixture was heated to 60° C. for 2 h after which time LCMS indicated clean conversion to the desired product. The reaction was diluted with EtOAc, washed with water then brine and the organic layer dried (MgSO4), filtered and the solvent removed in vacuo to give the desired compound an off white solid, 550 mg, 78% yield.

Sources & evidence

ORD record
ord-67d78661df944640bd8ecb4789f31215
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

Loading…