Morpholine → HCID 58941677, compound

HRID 13720Notes

Reaction equation

HRID 13720 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7]([C:15]1[C:23]3[C:18](=[C:19]([NH:24][S:25]([CH3:28])(=[O:27])=[O:26])[CH:20]=[CH:21][CH:22]=3)[NH:17][CH:16]=1)([CH2:11][CH2:12][CH2:13]I)[CH2:6][CH2:5]2.[NH:29]1[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1>O1CCCC1>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7]([C:15]1[C:23]3[C:18](=[C:19]([NH:24][S:25]([CH3:28])(=[O:27])=[O:26])[CH:20]=[CH:21][CH:22]=3)[NH:17][CH:16]=1)([CH2:11][CH2:12][CH2:13][N:29]1[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1)[CH2:6][CH2:5]2

Participants

4

Reactant 2

HCID 8083MorpholineHCID 68583228HCID 68583228, compound

Product 1

HCID 58941677HCID 58941677, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Combine N-{3-[5-fluoro-1-(3-iodo-propyl)-indan-1-yl]-1H-indol-7-yl}-methane sulfonamide (65 mg, 0.13 mmol) and morpholine (2 ml) in anhydrous tetrahydrofuran (2.5 ml) and stir at room temperature under nitrogen overnight. Remove the volatiles under high vacuum, dissolve the residue in dichloromethane, add solid potassium carbonate, stir for ten minutes, filter, and concentrate in vacuo. Purify the residue on silica eluting with 5 to 10% methanol in dichloromethane over 15 minutes to obtain the title compound as a white solid (50 mg, 83%). LC-MS m/z 472.2 (M++1).

Workup

  1. customRemove the volatiles under high vacuum
  2. dissolutiondissolve the residue in dichloromethane
  3. additionadd solid potassium carbonate
  4. filtrationfilter
  5. concentrationconcentrate in vacuo
  6. customPurify the residue on silica eluting with 5 to 10% methanol in dichloromethane over 15 minutes

Sources & evidence

ORD record
ord-c8227624ae074178afc6c8c2d45e4807
Source dataset
uspto-grants-2010_06
Patent number
US07728150B2

Reaction notes

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