N, N-dimethyl-(1-iodoethoxy)carbonyloxyacetamide → {1-[(1-Carbamoyl-6-chloro-5-fluoro-2-oxo-1,2-dihydro-indol-3-ylidene)-thiophen-2-ylmethoxy]-ethoxycarbonyloxy}-N,N-dimethylacetamide

HRID 326782Notes

Reaction equation

HRID 326782 reaction equation
[OH:1][C:2]([C:18]1[S:19][CH:20]=[CH:21][CH:22]=1)=[C:3]1[C:11]2[C:6](=[CH:7][C:8]([Cl:13])=[C:9]([F:12])[CH:10]=2)[N:5]([C:14]([NH2:16])=[O:15])[C:4]1=[O:17].[CH3:23][N:24]([CH3:35])[C:25](=[O:34])[CH2:26][O:27][C:28]([O:30][CH:31](I)[CH3:32])=[O:29]>CC(C)=O>[C:14]([N:5]1[C:6]2[C:11](=[CH:10][C:9]([F:12])=[C:8]([Cl:13])[CH:7]=2)[C:3](=[C:2]([C:18]2[S:19][CH:20]=[CH:21][CH:22]=2)[O:1][CH:31]([O:30][C:28]([O:27][CH2:26][C:25]([N:24]([CH3:23])[CH3:35])=[O:34])=[O:29])[CH3:32])[C:4]1=[O:17])(=[O:15])[NH2:16]

Participants

4

Reactant 2

HCID 19735923N, N-dimethyl-(1-iodoethoxy)carbonyloxyacetamideHCID 178514064HCID 178514064, compound

Product 1

HCID 54112031{1-[(1-Carbamoyl-6-chloro-5-fluoro-2-oxo-1,2-dihydro-indol-3-ylidene)-thiophen-2-ylmethoxy]-ethoxycarbonyloxy}-N,N-dimethylacetamideYield 8.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The tetrabutylammonium salt of 3-[hydroxy-(2-thienyl)methylene]-6-chloro-5-fluoro-2,3-dihydro-2-oxo-1H-indole-1-carboxamide (6.25 g) and N, N-dimethyl-(1-iodoethoxy)carbonyloxyacetamide (5.55 g) were combined in 60 mL of acetone, and the solution stirred for 90 hr. at 20° C. The precipitate present was removed by filtration and dried in vacuo. The solids were chromatographed on silica gel, eluting with 90:10 chloroform:acetone. Fractions containing the title product were combined and evaporated. The residue was slurried with a small amount of ethyl ether and filtered to give 820 mg of yellow solid, mp 194.5°-195.5° C.

Workup

  1. customat 20° C
  2. customThe precipitate present was removed by filtration
  3. customdried in vacuo
  4. customThe solids were chromatographed on silica gel
  5. washeluting with 90:10 chloroform
  6. additionFractions containing the title product
  7. customevaporated
  8. filtrationfiltered

Sources & evidence

ORD record
ord-9002f510ca894e4086c6643235f40631
Source dataset
uspto-grants-1993_12
Patent number
US05270331

Reaction notes

Loading…