Trifluoromethanesulfonic anhydride → HCID 22907266, compound

HRID 2258591Notes

Reaction equation

HRID 2258591 reaction equation
FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.O[CH2:17][CH2:18][CH2:19][N:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22]([C:29]2[C:30](=[O:45])[NH:31][C:32](=[O:44])[C:33]=2[C:34]2[C:42]3[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=3)[N:36]([CH3:43])[CH:35]=2)=[CH:21]1.[CH:46]1([NH2:49])[CH2:48][CH2:47]1>C(Cl)Cl.C1COCC1>[CH:46]1([NH:49][CH2:17][CH2:18][CH2:19][N:20]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:22]([C:29]3[C:30](=[O:45])[NH:31][C:32](=[O:44])[C:33]=3[C:34]3[C:42]4[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=4)[N:36]([CH3:43])[CH:35]=3)=[CH:21]2)[CH2:48][CH2:47]1

Participants

6

Reactant 3

HCID 67749Trifluoromethanesulfonic anhydrideHCID 69828CyclopropylamineHCID 5327929HCID 5327929, compound

Product 1

HCID 22907266HCID 22907266, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a 0° C. solution of trifluoromethanesulfonic acid anhydride (188 mg, 0.67 mmol) in dry methylene chloride (15 mL) was added a solution of 3-[1-(3-hydroxy-propyl)-1H-indol-3-yl)-4(1-methyl-1H-indol-3-yl)-pyrrole-2,5-dione (100 mg, 0.25 mmol) in THF (10 mL). After 2 hours, cyclopropylamine (200 μl, 5 mmol) was added and stirring continued over night. The reaction mixture was quenched with water. The organic phase was separated, washed with water (3×), dried, and evaporated. The residual red oil was purified by flash chromatography on silica gel eluting with a methylene chloride/ethanol gradient (98:2-95:5). Evaporation of the eluting solvent gave the title compound (70 mg, 64% yield).

Workup

  1. waitcontinued over night
  2. customThe reaction mixture was quenched with water
  3. customThe organic phase was separated
  4. washwashed with water (3×)
  5. customdried
  6. customevaporated
  7. customThe residual red oil was purified by flash chromatography on silica gel eluting with a methylene chloride/ethanol gradient (98:2-95:5)
  8. customEvaporation of the eluting solvent

Sources & evidence

ORD record
ord-fe6e57cb468d42458b6fbb4177bbd7e9
Source dataset
uspto-grants-1997_08
Patent number
US05661173

Reaction notes

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