Diisopropylethylamine → HCID 68443476, compound

HRID 1455557Notes

Reaction equation

HRID 1455557 reaction equation
CCN(C(C)C)C(C)C.[C:10]([O:14][C:15]([N:17]1[CH:22]2[CH2:23][CH2:24][CH:18]1[CH2:19][C:20](=[C:25]([C:28]([OH:30])=O)[C:26]#[N:27])[CH2:21]2)=[O:16])([CH3:13])([CH3:12])[CH3:11].[Br:31][C:32]1[C:33]([S:39]([NH2:42])(=[O:41])=[O:40])=[C:34]([Cl:38])[S:35][C:36]=1[Cl:37]>CN(C=O)C.CN(C1C=CN=CC=1)C.CC(N(C)C)=O>[C:10]([O:14][C:15]([N:17]1[CH:22]2[CH2:23][CH2:24][CH:18]1[CH2:19][C:20](=[C:25]([C:26]#[N:27])[C:28]([NH:42][S:39]([C:33]1[C:32]([Br:31])=[C:36]([Cl:37])[S:35][C:34]=1[Cl:38])(=[O:40])=[O:41])=[O:30])[CH2:21]2)=[O:16])([CH3:11])([CH3:12])[CH3:13]

Participants

7

Reactant 3

HCID 81531DiisopropylethylamineHCID 27403184-Bromo-2,5-dichloro-thiophene-3-sulfonamideHCID 68443024HCID 68443024, compound

Product 1

HCID 68443476HCID 68443476, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 31374DimethylacetamideSolvent

Procedure

120 μl of DIEA are added to a solution of 102 mg of 3-(carboxy-cyano-methylene)-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester, 162 mg of 4-bromo-2,5-dichloro-thiophene-3-sulfonamide, 583 μl of PPA in DMF (50%) and 43 mg of DMAP in 4 ml of DMA, and the mixture obtained is stirred at RT for 48 hours. From the mixture obtained solvent is removed in vacuo and the residue obtained is subjected to preparative HPLC on an RP-18 column. 3-[2-(4-Bromo-2,5-dichloro-thiophene-3-sulfonylamino)-1-cyano-2-oxo-ethylidene]-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester in the form of a foam is obtained.

Workup

  1. customFrom the mixture obtained solvent
  2. customis removed in vacuo
  3. customthe residue obtained

Sources & evidence

ORD record
ord-9f7e451d3f2d4cd6b0299e52a5d5eaa1
Source dataset
uspto-grants-2009_01
Patent number
US07482462B2

Reaction notes

Loading…