Water → HCID 11724186, compound

HRID 1737419Notes

Reaction equation

HRID 1737419 reaction equation
C1(C)C=CC(S(O[CH2:11][C@@H:12]2[O:26][C:16]3=[C:17]4[C:21](=[C:22]([CH3:24])[CH:23]=[C:15]3[O:14][CH2:13]2)[NH:20][C:19](=[O:25])[CH2:18]4)(=O)=O)=CC=1.[S:28]1[CH:32]=[CH:31][CH:30]=[C:29]1[CH2:33][NH2:34].O>CS(C)=O>[S:28]1[CH:32]=[CH:31][CH:30]=[C:29]1[CH2:33][NH:34][CH2:11][CH:12]1[O:26][C:16]2=[C:17]3[C:21](=[C:22]([CH3:24])[CH:23]=[C:15]2[O:14][CH2:13]1)[NH:20][C:19](=[O:25])[CH2:18]3

Participants

5

Reactant 3

HCID 962WaterHCID 34005(2-Thienylmethyl)amineHCID 86752623HCID 86752623, compound

Product 1

HCID 11724186HCID 11724186, compoundYield 31.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

(R)-2-(Toluene-4-sulfonyloxymethyl)-6-methyl-2,3,8,9-tetrahydro-7H-1,4-dioxino[2,3-e]indol-8-one (1.00 g,2.57 mmole) and thiophene-2-methylamine (1.42 g, 12.6 mmole) were combined in 15 ml of dry DMSO and heated to 90° C. for 6 hours under a nitrogen atmosphere. After cooling to room temperature, 250 ml of water was added and a brown solid precipitated This was dissolved in methylene chloride, dried over MgSO4, filtered and concentrated in vacuum to yield an flaky orange solid, which was column chromatographed on silica gel using 1.5% methanol/CH2Cl2 as eluant. The free base of the title compound (0.27 g) thus obtained was crystallized from isopropanol with the addition of fumaric acid (0.10 g, 0.90 mmole) to give 0.28 g of the (S) enantiomer of the title compound as a light orange solid fumarate, m.p. 211-212° C.

Workup

  1. temperatureAfter cooling to room temperature
  2. customa brown solid precipitated
  3. dissolutionThis was dissolved in methylene chloride
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuum
  7. customto yield an flaky orange solid, which
  8. customchromatographed on silica gel using 1.5% methanol/CH2Cl2 as eluant

Sources & evidence

ORD record
ord-9716c422c8344fe99ca7f38fe1ffe74d
Source dataset
uspto-grants-1999_10
Patent number
US05962465

Reaction notes

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