Acetic Acid → HCID 19844125, compound

HRID 2352309Notes

Reaction equation

HRID 2352309 reaction equation
O=C1C2C(=CC=CC=2)C(=O)N1CCCC=N[NH:17][C:18]1[CH:23]=[CH:22][C:21]([S:24]([NH:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)(=[O:26])=[O:25])=[CH:20][CH:19]=1.B(F)(F)F.[C:38]([O-:41])([O-])=O.[Na+].[Na+].[C:44]([OH:47])(=O)[CH3:45]>O>[O:47]=[C:44]1[C:45]2[C:30](=[CH:29][CH:28]=[CH:33][CH:32]=2)[C:38](=[O:41])[N:17]1[CH2:18][CH2:19][C:20]1[C:19]2[C:18](=[CH:23][CH:22]=[C:21]([S:24]([NH:27][C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)(=[O:25])=[O:26])[CH:20]=2)[NH:17][CH:21]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6356Boron trifluorideHCID 10340Sodium CarbonateHCID 70385996HCID 70385996, compound

Product 1

HCID 19844125HCID 19844125, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of the product of stage (i) (5.08 g) in glacial acetic acid (40 ml) containing boron trifluride, etherate (6.7 ml) was heated on a steam bath for 15 min, cooled, diluted with water (200 ml) basified (Na2CO3) and extracted with ethyl acetate (2×200 ml). The combined organic extracts were dried (MgSO4) and evaporated in vacuo to give crude 3-[2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)ethyl]-N-phenyl-1H-indole-5-sulphonamide as a foam (4.8 g). The foam was suspended in ethanol (100 ml) containing hydrazine hydrate (5 ml), heated at reflux for 2 h, cooled, the ethanol removed in vacuo and the residue partitioned between sodium carbonate (2 N, 150 ml) and ethyl acetate (2×150 ml). The combined organic extracts were dried (Na2SO4) and evaporated in vacuo to give a foam which was purified by flash chromatography eluted with dichloromethane:ethanol:ammonium hydroxide (20:5:0.2) to give the title compound free base (0.57 g) as a solid. The free base was dissolved in a solution of maleic acid (0.21 g) in methanol (10 ml), and the salt precipitated by the addiion of ethyl acetate (100 ml) and dry ether (300 ml). The salt was filtered off and dried in vacuo to give the title compound as a solid. (0.55 g) m.p. 145°-147°.

Workup

  1. temperaturewas heated on a steam bath for 15 min
  2. temperaturecooled
  3. extractionextracted with ethyl acetate (2×200 ml)
  4. dry with materialThe combined organic extracts were dried (MgSO4)
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-04a1f585aa6d441dab2e3614d1d88951
Source dataset
uspto-grants-1989_10
Patent number
US04876267

Reaction notes

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