1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 4-(Furo[3,2-c]pyridine-2-carbonylsulfanyl)piperidine-1-carboxylic acid tert-butyl ester

HRID 217178

Reaction equation

HRID 217178 reaction equation
CCN=C=NCCCN(C)C.[O:12]1[C:20]2[CH:19]=[CH:18][N:17]=[CH:16][C:15]=2[CH:14]=[C:13]1[C:21]([OH:23])=O.[C:24]([O:28][C:29]([N:31]1[CH2:36][CH2:35][CH:34]([SH:37])[CH2:33][CH2:32]1)=[O:30])([CH3:27])([CH3:26])[CH3:25]>CN(C=O)C.CN(C1C=CN=CC=1)C>[C:24]([O:28][C:29]([N:31]1[CH2:36][CH2:35][CH:34]([S:37][C:21]([C:13]2[O:12][C:20]3[CH:19]=[CH:18][N:17]=[CH:16][C:15]=3[CH:14]=2)=[O:23])[CH2:33][CH2:32]1)=[O:30])([CH3:27])([CH3:25])[CH3:26]

Participants

6

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 13803073Furo(3,2-c)pyridine-2-carboxylic acidHCID 21906090tert-Butyl 4-sulfanylpiperidine-1-carboxylate

Product 1

HCID 114942624-(Furo[3,2-c]pyridine-2-carbonylsulfanyl)piperidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent2×

Procedure

A solution of EDCI (66 mg, 0.35 mmol) in anhydrous DMF (2 mL) was added to a stirred solution of furo[3,2-c]pyridine-2-carboxylic acid (45 mg, 0.28 mmol) in anhydrous DMF (1 mL). After 1 h, the mixture was treated with a solution of DMAP (6 mg, 0.05 mmol) and 4-mercaptopiperidine-1-carboxylic acid tert-butyl ester (50 mg, 0.23 mmol), before being stirred for an additional 16 h. The DMF was removed under reduced pressure, then the residue was purified by flash chromatography (IH-EtOAc, 1:1 to 3:7) to furnish the title compound: RT=3.34 min; m/z (ES+)=363.1 [M+H]+.

Workup

  1. customThe DMF was removed under reduced pressure
  2. customthe residue was purified by flash chromatography (IH-EtOAc, 1:1 to 3:7)

Sources & evidence

ORD record
ord-5df15699678c42798a3686af9fe6a4b0
Source dataset
uspto-grants-2012_06
Patent number
US08193359B2

Linked notes

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