1,2-Dichloroethane → 4-(4-Bromo-2,5-dichloro-thiophene-3-sulfonylaminocarbonyl)-piperidine-1-carboxylic acid tert-butyl ester

HRID 1455542Notes

Reaction equation

HRID 1455542 reaction equation
CCN(C(C)C)C(C)C.C(Cl)CCl.[Br:14][C:15]1[C:16]([S:22]([NH2:25])(=[O:24])=[O:23])=[C:17]([Cl:21])[S:18][C:19]=1[Cl:20].[C:26]([O:30][C:31]([N:33]1[CH2:38][CH2:37][CH:36]([C:39](O)=[O:40])[CH2:35][CH2:34]1)=[O:32])([CH3:29])([CH3:28])[CH3:27]>CN(C1C=CN=CC=1)C.CN(C=O)C>[C:26]([O:30][C:31]([N:33]1[CH2:38][CH2:37][CH:36]([C:39]([NH:25][S:22]([C:16]2[C:15]([Br:14])=[C:19]([Cl:20])[S:18][C:17]=2[Cl:21])(=[O:23])=[O:24])=[O:40])[CH2:35][CH2:34]1)=[O:32])([CH3:29])([CH3:28])[CH3:27]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 81531DiisopropylethylamineHCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acidHCID 27403184-Bromo-2,5-dichloro-thiophene-3-sulfonamide

Product 1

HCID 115192584-(4-Bromo-2,5-dichloro-thiophene-3-sulfonylaminocarbonyl)-piperidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

60 mg of DMAP, 130 mg of DIEA and 192 mg of EDC are added to a solution of 155 mg of 4-bromo-2,5-dichloro-thiophene-3-sulfonamide and 230 mg of 1-(tert.butyloxycarbonyl)-piperidine-4-carboxylic acid in 8 ml of DMF. The mixture obtained is stirred for ca. 16 h at ca. 30°, solvent is evaporated and the evaporation residue is treated with EtAc. The mixture obtained is washed with aqueous 1 N HCl, aqueous saturated NaHCO3 and brine, and dried. Solvent from the organic phase obtained is evaporated and the evaporation residue is subjected to chromatography. 4-(4-Bromo-2,5-dichloro-thiophene-3-sulfonylaminocarbonyl)-piperidine-1-carboxylic acid tert.-butyl ester is obtained and lyophilized from 1,4-dioxane.

Workup

  1. customThe mixture obtained
  2. customsolvent is evaporated
  3. additionthe evaporation residue is treated with EtAc
  4. customThe mixture obtained
  5. washis washed with aqueous 1 N HCl, aqueous saturated NaHCO3 and brine
  6. customdried
  7. customSolvent from the organic phase obtained
  8. customis evaporated

Sources & evidence

ORD record
ord-9404c1f99dc6473c96cb5790a665bc33
Source dataset
uspto-grants-2009_01
Patent number
US07482462B2

Reaction notes

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