Hydrochloric Acid → HCID 19045473, compound

HRID 1781420Notes

Reaction equation

HRID 1781420 reaction equation
[CH3:1][S:2]([Cl:5])(=[O:4])=[O:3].[NH:6]1[C:14]2[C:9](=[CH:10][C:11]([CH2:15][CH2:16][N:17]3[CH2:22][CH2:21][C:20]4([CH2:27][C:26](=[O:28])[C:25]5[CH:29]=[C:30]([NH:33][S:34]([CH3:37])(=[O:36])=[O:35])[CH:31]=[CH:32][C:24]=5[O:23]4)[CH2:19][CH2:18]3)=[CH:12][CH:13]=2)[CH2:8][CH2:7]1.Cl.[N:39]1C=CC=CC=1>C(O)C>[ClH:5].[CH3:1][S:2]([NH:39][N:6]1[C:14]2[C:9](=[CH:10][C:11]([CH2:15][CH2:16][N:17]3[CH2:18][CH2:19][C:20]4([CH2:27][C:26](=[O:28])[C:25]5[CH:29]=[C:30]([NH:33][S:34]([CH3:37])(=[O:35])=[O:36])[CH:31]=[CH:32][C:24]=5[O:23]4)[CH2:21][CH2:22]3)=[CH:12][CH:13]=2)[CH2:8][CH2:7]1)(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 19045408HCID 19045408, compound

Product 1

HCID 19045473HCID 19045473, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methanesulfonyl chloride (55 mg, 0.48 mmol) was added to a suspension of 3,4-dihydro-1'-[2-(2,3-dihydro-1H-indol-5-yl)ethyl]-6-methanesulfonamido-spiro[(2H)-benzopyran-2,4'-piperidine]-4-one (crude, 84% pure, 217 mg, 0.4 mmol) in pyridine (5 ml). The mixture was stirred for 22 hours, then the solvent was evaporated under reduced pressure. Aqueous sodium hydrogen carbonate (saturated, 20 ml) and water (5 ml) were added and the mixture was extracted with dichloromethane (3×25 ml). The combined organic fractions were dried (Na2SO4) and evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with CH2Cl2 /MeOH/NH3 (Aq.) (96:4:0.4) to give a yellow glass which was suspended in ethanol (5 ml) and treated with ethanolic HCl (6N, 0.5 ml). The mixture was stirred for 1 hr, cooled and the precipitate was collected and dried in vacuo to give the hydrochloride as a white solid (91 mg, 40%), m.p.>285° C.

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. additionAqueous sodium hydrogen carbonate (saturated, 20 ml) and water (5 ml) were added
  3. extractionthe mixture was extracted with dichloromethane (3×25 ml)
  4. dry with materialThe combined organic fractions were dried (Na2SO4)
  5. customevaporated under reduced pressure
  6. customThe residue was purified by flash column chromatography on silica gel
  7. washeluting with CH2Cl2 /MeOH/NH3 (Aq.) (96:4:0.4)
  8. customto give a yellow glass which
  9. stirringThe mixture was stirred for 1 hr
  10. temperaturecooled
  11. customthe precipitate was collected
  12. customdried in vacuo

Sources & evidence

ORD record
ord-f8aaccce3b704807855d9507b5581a57
Source dataset
uspto-grants-1997_05
Patent number
US05633247

Reaction notes

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