[[(Aminooxy)carbonyl](methyl)amino]methane hydrochloride → [(Z)-[3-[[2-(4-fluorophenyl)-2-hydroxyethyl]-methylsulfamoyl]-5,6-dihydro-4H-1-benzothiophen-7-ylidene]amino] N,N-dimethylcarbamate

HRID 1351330Notes

Reaction equation

HRID 1351330 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:25])[CH2:9][N:10]([CH3:24])[S:11]([C:14]2[C:15]3[CH2:22][CH2:21][CH2:20][C:19](=O)[C:16]=3[S:17][CH:18]=2)(=[O:13])=[O:12])=[CH:4][CH:3]=1.Cl.[NH2:27][O:28][C:29]([N:31]([CH3:33])[CH3:32])=[O:30]>C(O)(=O)C>[CH3:32][N:31]([CH3:33])[C:29]([O:28]/[N:27]=[C:19]1/[CH2:20][CH2:21][CH2:22][C:15]2[C:14]([S:11]([N:10]([CH2:9][CH:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[OH:25])[CH3:24])(=[O:12])=[O:13])=[CH:18][S:17][C:16]/1=2)=[O:30]

Participants

4

Reactant 2

HCID 21098721[[(Aminooxy)carbonyl](methyl)amino]methane hydrochlorideHCID 77617953HCID 77617953, compound

Product 1

HCID 11431333[(Z)-[3-[[2-(4-fluorophenyl)-2-hydroxyethyl]-methylsulfamoyl]-5,6-dihydro-4H-1-benzothiophen-7-ylidene]amino] N,N-dimethylcarbamate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

7-Oxo-4,5,6,7-tetrahydro-benzo[b]thiophene-3-sulfonic acid [2-(4-fluorophenyl)-2-hydroxyethyl]-methyl-amide (the compound of Preparation Example 48) (60 mg) and [[(aminooxy)carbonyl](methyl)amino]methane hydrochloride (the compound of Preparation Example 122) (24 mg) were stirred in acetic acid at 50° C. for 3 hours. The residue resulting from the removal of the solvent by evaporation was purified by silica gel column chromatography (hexane/ethyl acetate). Among the two spots that were identifeid by developing the reaction solution by TLC (solvent system was hexane:ethyl acetate=1:3), the fraction of the compound with a high polarity (low Rf value) was collected, and the title compound (9 mg) was obtained as a colorless amorphous substance.

Workup

  1. customthe compound of Preparation Example 122) (24 mg)
  2. customThe residue resulting from the removal of the solvent by evaporation
  3. customwas purified by silica gel column chromatography (hexane/ethyl acetate)
  4. customthe fraction of the compound with a high polarity (low Rf value) was collected

Sources & evidence

ORD record
ord-79074fe338cd44a7bda11ac704c23b0e
Source dataset
uspto-grants-2007_05
Patent number
US07217723B2

Reaction notes

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