Triethylamine → (+/-)-cis-N-(5-Chloro-1-phenylsulfonylindole-2-sulfonyl)-1,2-cyclopentanediamine

HRID 459467Notes

Reaction equation

HRID 459467 reaction equation
[C@@H:1]1([NH2:7])[CH2:5][CH2:4][CH2:3][C@@H:2]1[NH2:6].C(N(CC)CC)C.ClC1C=C2C(=CC=1)N(C1C=CC=CC=1)C(S(Cl)(=O)=O)C2=S(=O)=O.[Cl:38][C:39]1[CH:40]=[C:41]2[C:45](=[CH:46][CH:47]=1)[N:44]([S:48]([C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)(=[O:50])=[O:49])[C:43]([S:57](Cl)(=[O:59])=[O:58])=[CH:42]2>ClCCl.O>[Cl:38][C:39]1[CH:40]=[C:41]2[C:45](=[CH:46][CH:47]=1)[N:44]([S:48]([C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)(=[O:49])=[O:50])[C:43]([S:57]([NH:6][C@@H:2]1[CH2:3][CH2:4][CH2:5][C@@H:1]1[NH2:7])(=[O:59])=[O:58])=[CH:42]2

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 11412654cis-Cyclopentane-1,2-diamineHCID 235137375-Chloro-1-phenylsulfonylindole-2-sulfonyl chloride2×HCID 865930565-chloro-1-phenyl-3-sulfonyl-2H-indole-2-sulfonyl chloride

Product 1

HCID 18442845(+/-)-cis-N-(5-Chloro-1-phenylsulfonylindole-2-sulfonyl)-1,2-cyclopentanediamineYield 407.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

cis-1,2-Cyclopentanediamine (WO98/30574) (348 mg) was dissolved in dichloromethane (10 ml), and to the solution triethylamine (1 ml) and 5-chloro-1-phenyl-sulfonylindole-2-sulfonyl chloride (390 mg) were added at 0° C. with stirring. After 15 minutes and 1 hour, 5-chloro-1-phenylsulfonylindole-2-sulfonyl chloride (156 mg) was additionally added. After stirring for 15 minutes, 5-chloro-1-phenylsulfonylindole-2-sulfonyl chloride (78 mg) was further added, and the mixture was stirred at room temperature for 2 hours. Water was added to the reaction mixture to separate an organic layer. The resultant organic layer was washed with a saturated solution of sodium hydrogencarbonate and dried over anhydrous sodium sulfate. The residue was purified by flash column chromatography on silica gel (chloroform:methanol=23:2) to obtain the title compound (739 mg) as a pale yellow solid.

Workup

  1. stirringAfter stirring for 15 minutes
  2. stirringthe mixture was stirred at room temperature for 2 hours
  3. customto separate an organic layer
  4. washThe resultant organic layer was washed with a saturated solution of sodium hydrogencarbonate
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe residue was purified by flash column chromatography on silica gel (chloroform:methanol=23:2)

Sources & evidence

ORD record
ord-fa9b32c2f4414841805c0ee2d9939cea
Source dataset
uspto-grants-2007_03
Patent number
US07192968B2

Reaction notes

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