Dimethylformamide → 2-[4-Methylsulfanyl-3-(2-m-tolyl-ethoxy)-benzoylamino]-indane-2-carboxylic acid methyl ester

HRID 2405204Notes

Reaction equation

HRID 2405204 reaction equation
[CH3:1][S:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][C:4]=1[O:12][CH2:13][CH2:14][C:15]1[CH:16]=[C:17]([CH3:21])[CH:18]=[CH:19][CH:20]=1.CN(C=O)C.C(Cl)(=O)C(Cl)=O.Cl.[CH3:34][O:35][C:36]([C:38]1([NH2:47])[CH2:46][C:45]2[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=2)[CH2:39]1)=[O:37].C(=O)([O-])O.[Na+]>C(Cl)Cl.CC(=O)OCC>[CH3:34][O:35][C:36]([C:38]1([NH:47][C:7](=[O:9])[C:6]2[CH:10]=[CH:11][C:3]([S:2][CH3:1])=[C:4]([O:12][CH2:13][CH2:14][C:15]3[CH:16]=[C:17]([CH3:21])[CH:18]=[CH:19][CH:20]=3)[CH:5]=2)[CH2:46][C:45]2[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=2)[CH2:39]1)=[O:37]

Participants

8

Reactant 5

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 516892Sodium BicarbonateHCID 45074056methyl 2-amino-2,3-dihydro-1H-indene-2-carboxylate hydrochlorideHCID 670765594-Methylsulfanyl-3-(2-m-tolyl-ethoxy)-benzoic acid

Product 1

HCID 670766742-[4-Methylsulfanyl-3-(2-m-tolyl-ethoxy)-benzoylamino]-indane-2-carboxylic acid methyl esterYield 93.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

The compound of step 3 (395 mg, 1.31 mmol) was dissolved in DCM (5 ml). DMF (29 mg, 0.39 mmol) and oxalyl chloride (3.9 ml of a 2 M solution in DCM) were added at room temperature. The mixture was stirred for 60 min, evaporated to dryness in vacuo, dissolved in dioxane and evaporated again. The residue was dissolved in DCM (2 ml) and the solution was slowly added with stirring to an ice-cooled mixture of 2-amino-indane-2-carboxylic acid methyl ester hydrochloride (5.42 g, 23.8 mmol), EA and an excess of saturated aqueous sodium hydrogencarbonate solution. After 2 h, the organic layer was separated, washed with a saturated sodium chloride solution, dried over sodium sulfate, filtered and evaporated to dryness. 582 mg of the title compound were obtained.

Workup

  1. customevaporated to dryness in vacuo
  2. dissolutiondissolved in dioxane
  3. customevaporated again
  4. dissolutionThe residue was dissolved in DCM (2 ml)
  5. additionthe solution was slowly added
  6. stirringwith stirring to an ice-
  7. temperaturecooled
  8. waitAfter 2 h
  9. customthe organic layer was separated
  10. washwashed with a saturated sodium chloride solution
  11. dry with materialdried over sodium sulfate
  12. filtrationfiltered
  13. customevaporated to dryness

Sources & evidence

ORD record
ord-2475a41c2a8d481a9e3964f0b3f40741
Source dataset
uspto-grants-2014_08
Patent number
US08802720B2

Reaction notes

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