1,8-Diazabicyclo(5.4.0)undec-7-ene → 6-(Propane-2-sulfonylamino)-4'-[3-(propane-2-sulfonylamino)-thiophen-2-yl]-biphenyl-2-carboxylic acid methyl ester

HRID 746784Notes

Reaction equation

HRID 746784 reaction equation
N12CCCN=C1CCCCC2.[CH3:12][O:13][C:14]([C:16]1[C:17]([C:23]2[CH:28]=[CH:27][C:26]([C:29]3[S:30][CH:31]=[CH:32][C:33]=3[NH:34][S:35]([CH:38]([CH3:40])[CH3:39])(=[O:37])=[O:36])=[CH:25][CH:24]=2)=[C:18]([NH2:22])[CH:19]=[CH:20][CH:21]=1)=[O:15].[CH:41]([S:44](Cl)(=[O:46])=[O:45])([CH3:43])[CH3:42]>ClCCl>[CH3:12][O:13][C:14]([C:16]1[C:17]([C:23]2[CH:24]=[CH:25][C:26]([C:29]3[S:30][CH:31]=[CH:32][C:33]=3[NH:34][S:35]([CH:38]([CH3:40])[CH3:39])(=[O:37])=[O:36])=[CH:27][CH:28]=2)=[C:18]([NH:22][S:44]([CH:41]([CH3:43])[CH3:42])(=[O:46])=[O:45])[CH:19]=[CH:20][CH:21]=1)=[O:15]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 824082-Propanesulfonyl chlorideHCID 692534626-Amino-4'-[3-(propane-2-sulfonylamino)-thiophen-2-yl]-biphenyl-2-carboxylic acid methyl ester

Product 1

HCID 692513426-(Propane-2-sulfonylamino)-4'-[3-(propane-2-sulfonylamino)-thiophen-2-yl]-biphenyl-2-carboxylic acid methyl esterYield 19.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add 1,8-diazabicyclo [5.4.0] undec-7-ene (DBU) drop wise (0.51 mL, 3.6 mmol) to a suspension of 6-amino-4′-[3-(propane-2-sulfonylamino)-thiophen-2-yl]-biphenyl-2-carboxylic acid methyl ester (208 mg 0.48 mmol) in dichloromethane (9 ml) at 0° C., followed by drop wise addition of isopropylsulfonyl chloride (0.21 mL, 0.9 mmol) and stir the reaction at room temperature overnight. Remove solvent under reduced pressure. Purify with flash chromatography (Silica gel-hexane/EtOAc). Concentrate the desired fractions to provide 6-(propane-2-sulfonylamino)-4′-[3-(propane-2-sulfonylamino)-thiophen-2-yl]-biphenyl-2-carboxylic acid methyl ester (50 mg). MS (m/e): 535.1(M−1).

Workup

  1. customthe reaction at room temperature overnight
  2. customPurify with flash chromatography (Silica gel-hexane/EtOAc)
  3. concentrationConcentrate the desired fractions

Sources & evidence

ORD record
ord-e8a52a4ce8bb46388ef9eb264187ece2
Source dataset
uspto-grants-2008_07
Patent number
US07393868B2

Reaction notes

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