1,1'-Carbonyldiimidazole → HCID 17786696, compound

HRID 618813Notes

Reaction equation

HRID 618813 reaction equation
[CH3:1][S:2]([N:5]([CH:13]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([CH3:23])[CH:21]=2)[O:16][C:15]([CH3:25])([CH3:24])[CH2:14]1)[CH2:6][CH2:7][CH2:8][CH2:9][C:10](O)=[O:11])(=[O:4])=[O:3].C1N=CN(C(N2C=NC=C2)=O)C=1.[NH2:38][CH2:39][CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][N:42]=1>C1COCC1>[N:42]1[CH:43]=[CH:44][CH:45]=[CH:46][C:41]=1[CH2:40][CH2:39][NH:38][C:10](=[O:11])[CH2:9][CH2:8][CH2:7][CH2:6][N:5]([S:2]([CH3:1])(=[O:3])=[O:4])[CH:13]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([CH3:23])[CH:21]=2)[O:16][C:15]([CH3:25])([CH3:24])[CH2:14]1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 759192-PyridineethanamineHCID 21848627HCID 21848627, compound

Product 1

HCID 17786696HCID 17786696, compoundYield 49.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 0.5 g (1.4 mmol) of 5-[methylsulfonyl-(2,2,6-trimethylchroman-4-yl)amino]pentanoic acid (Example 10c) and 0.26 g (1.6 mmol) of CDI in 20 ml of THF is stirred at RT for 3 h. 0.2 g (1.6 mmol) of 2-(2-aminoethyl)-pyridine is then added and the mixture is stirred further overnight at RT. After concentrating the reaction mixture, the residue is taken up in EA and water, and the organic phase is washed 3 times with 2M sodium hydroxide solution. After drying over magnesium sulfate, concentration and purification by chromatography on silica gel using methylene chloride/methanol 9:1, 0. 0.33 g of 5-[methylsulfonyl-(2,2,6-trimethylchroman-4-yl)amino]-pentanoic acid (2-(2-pyridyl)ethyl)amide is obtained.

Workup

  1. stirringthe mixture is stirred further overnight at RT
  2. concentrationAfter concentrating the reaction mixture
  3. washwater, and the organic phase is washed 3 times with 2M sodium hydroxide solution
  4. dry with materialAfter drying over magnesium sulfate, concentration and purification by chromatography on silica gel

Sources & evidence

ORD record
ord-40a20c4aef55483aa9995e391086f282
Source dataset
uspto-grants-1999_09
Patent number
US05955607

Reaction notes

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