Benzenesulfonyl chloride → HCID 11683343, compound

HRID 853901Notes

Reaction equation

HRID 853901 reaction equation
[CH3:1][C:2]1([CH3:21])[CH2:20][N:6]2[C:7]3[CH:8]=[CH:9][C:10]([NH2:19])=[CH:11][C:12]=3[C:13]3([O:18][CH2:17][CH2:16][CH2:15][O:14]3)[C:5]2=[N:4][CH2:3]1.CCN(CC)CC.[C:29]1([S:35](Cl)(=[O:37])=[O:36])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>C(Cl)Cl>[CH3:1][C:2]1([CH3:21])[CH2:20][N:6]2[C:7]3[CH:8]=[CH:9][C:10]([NH:19][S:35]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)(=[O:37])=[O:36])=[CH:11][C:12]=3[C:13]3([O:18][CH2:17][CH2:16][CH2:15][O:14]3)[C:5]2=[N:4][CH2:3]1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 11616224HCID 11616224, compound

Product 1

HCID 11683343HCID 11683343, compoundYield 71.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3′,3′-dimethyl-3′,4′-dihydro-2′H-spiro[1,3-dioxane-2,10′-pyrimido[1,2-a]indol]-8′amine (0.060 g 0.21 mmol, 1 eq) in CH2Cl2 (2 mL) was added Et3N (0.060 mL, 0.43 mmol, 2.05 eq) and benzenesulfonyl chloride (0.030 mL, 0.23 mmol, 1.07 eq). The reaction was stirred at rt 1 hour and concentrated. The crude residue purified by column chromatography using acetone/hexanes (30/70) as an eluent to give the title compound as a white solid (0.064 g, 71%). NMR (400 Mz, DMSO-d6): consistent

Workup

  1. concentrationconcentrated
  2. customThe crude residue purified by column chromatography

Sources & evidence

ORD record
ord-da1bafdea747454a8484ce13344b30d9
Source dataset
uspto-grants-2007_08
Patent number
US07256198B2

Reaction notes

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