Sodium Chloride → HCID 11682171, compound

HRID 853902Notes

Reaction equation

HRID 853902 reaction equation
[CH3:1][C:2]1([CH3:30])[CH2:29][N:6]2[C:7]3[CH:8]=[CH:9][C:10]([NH:19][S:20]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)(=[O:22])=[O:21])=[CH:11][C:12]=3[C:13]3(OCCC[O:14]3)[C:5]2=[N:4][CH2:3]1.CS(O)(=O)=O.[Na+].[Cl-]>C(Cl)Cl.[Cl-].[Na+].O>[CH3:1][C:2]1([CH3:30])[CH2:29][N:6]2[C:7]3[CH:8]=[CH:9][C:10]([NH:19][S:20]([C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=4)(=[O:21])=[O:22])=[CH:11][C:12]=3[C:13](=[O:14])[C:5]2=[N:4][CH2:3]1

Participants

6

Reactant 3

HCID 5234Sodium ChlorideHCID 6395Methanesulfonic AcidHCID 11683343HCID 11683343, compound

Product 1

HCID 11682171HCID 11682171, compoundYield 61.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of N-(3′,3′-dimethyl-3′,4′-dihydro-2′H-spiro[1,3-dioxane-2,10′-pyrimido[1,2-a]indol]-8′-yl)benzenesulfonamide (0.064 g, 0.14 mmol, 1 eq) in CH2Cl2 (4 mL) was added methanesulfonic acid (2 mL). The reaction was stirred at rt overnight and then poured into brine. It was basified to pH 10, saturated with solid NaCl, and extracted with EtOAc. The combined organics were dried over sodium sulfate and concentrated. The crude residue purified by column chromatography using acetone/hexanes (40/60) as an eluent to give the title compound as a yellow foam (0.032 g, 58% ). NMR (400 Mz, DMSO-d6): consistent. MS: (ES−) m/z 368 [M−H].

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe combined organics were dried over sodium sulfate
  3. concentrationconcentrated
  4. customThe crude residue purified by column chromatography

Sources & evidence

ORD record
ord-400067b40e4543acaa2791b439cc2248
Source dataset
uspto-grants-2007_08
Patent number
US07256198B2

Reaction notes

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