1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 86613180, compound

HRID 746802Notes

Reaction equation

HRID 746802 reaction equation
N12CCCN=C1CCCCC2.[NH2:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20]1[CH:25]=[CH:24][C:23]([C:26]2[S:27][CH:28]=[CH:29][C:30]=2[NH:31][S:32]([CH:35]([CH3:37])[CH3:36])(=[O:34])=[O:33])=[CH:22][CH:21]=1.[CH:38]([S:41](Cl)(=[O:43])=[O:42])([CH3:40])[CH3:39]>ClCCl>[CH3:39][CH:38]([S:41]([NH:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20]1[CH:25]=[CH:24][C:23]([C:26]2[S:27][CH:28]=[CH:29][C:30]=2[NH:31][S:32]([CH:35]([CH3:37])[CH3:36])(=[O:34])=[O:33])=[CH:22][CH:21]=1)(=[O:43])=[O:42])[CH3:40]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 824082-Propanesulfonyl chlorideHCID 86613181HCID 86613181, compound

Product 1

HCID 86613180HCID 86613180, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add 1,8-diazabicyclo [5.4.0] undec-7-ene (DBU) drop wise (85 mg, 0.6 mmol) to a suspension of propane-2-sulfonic acid [2-(2′-aminomethyl-biphenyl-4-yl)-thiophen-3-yl]-amide (57 mg, 0.15 mmol) in dichloromethane (2 ml) at 0° C., followed by drop wise addition of isopropylsulfonyl chloride (42 mg, 0.3 mmol) and stir the reaction at room temperature overnight. Remove solvent under reduce pressure. Purify with flash chromatography (Silica gel-hexane/EtOAc). Concentrate the desired fractions to provide propane-2-sulfonic acid (2-{2′-[(propane-2-sulfonylamino)-methyl]-biphenyl-4-yl}-thiophen-3-yl)-amide. MS (m/e): 491.1(M−1), propane-2-sulfonic acid (2-{2′,2′-bis-[(propane-2-sulfonylamino)-methyl]-biphenyl-4-yl}-thiophen-3-yl)-amide. MS (m/e): 510.2(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-0510e15f9ebb4955b9e01ee26d5de4a5
Source dataset
uspto-grants-2008_07
Patent number
US07393868B2

Reaction notes

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