Dicyclohexylcarbodiimide → HCID 10280007, compound

HRID 2223899Notes

Reaction equation

HRID 2223899 reaction equation
[C:1]1([CH3:33])[CH:6]=[CH:5][C:4]([N:7]([CH:15]2[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][C:23]3([CH2:29][C:30](O)=[O:31])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)[CH2:17][CH2:16]2)[C:8]([C:10]2[O:11][CH:12]=[CH:13][CH:14]=2)=[O:9])=[CH:3][CH:2]=1.[CH3:34][S:35]([NH2:38])(=[O:37])=[O:36].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.ClCCl>[CH3:34][S:35]([NH:38][C:30]([CH2:29][C:23]1([CH2:22][CH2:21][N:18]2[CH2:19][CH2:20][CH:15]([N:7]([C:4]3[CH:3]=[CH:2][C:1]([CH3:33])=[CH:6][CH:5]=3)[C:8]([C:10]3[O:11][CH:12]=[CH:13][CH:14]=3)=[O:9])[CH2:16][CH2:17]2)[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1)=[O:31])(=[O:37])=[O:36]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 72879MethanesulfonamideHCID 10275841HCID 10275841, compound

Product 1

HCID 10280007HCID 10280007, compoundYield 98.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

[1-[2-[4-[N-(p-Tolyl)-2-furancarboxamido]-piperidin-1-yl]ethyl]cyclohexyl]acetic acid (synthesized in Example 3B-1) (203 mg), methanesulfonamide (84 mg), 1,3-dicyclohexylcarbodiimide (101 mg) and 4-dimethylaminopyridine (59 mg) were dissolved in dichloromethane (5 mL). The solution was stirred at room temperature for 4 days. The reaction solution was concentrated under reduced pressure. The resulting residue was purified by chromatography [silica gel, dichloromethane-methanol (10:1)] to give the title compound (233 mg).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. customThe resulting residue was purified by chromatography [silica gel, dichloromethane-methanol (10:1)]

Sources & evidence

ORD record
ord-f8c1283639464645b131d81155ebd262
Source dataset
uspto-grants-2008_05
Patent number
US07375115B2

Reaction notes

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