Dicyclohexylcarbodiimide → HCID 15843916, compound

HRID 1595932Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]2[CH:13]=[C:12]([C:14]([OH:16])=O)[CH:11]=[CH:10][N:9]=2)[CH:3]=1.Cl.[CH2:18]([NH2:21])[C:19]#[CH:20].C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.C1CCC(N=C=NC2CCCCC2)CC1>CN(C=O)C>[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]2[CH:13]=[C:12]([C:14]([NH:21][CH2:18][C:19]#[CH:20])=[O:16])[CH:11]=[CH:10][N:9]=2)[CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

4′-Methyl-2,2′-bipyridine-4-carboxylic acid (0.22 g, 1 mmol), propargylamine hydrochloride (0.092 g, 1 mmol), HOBt (0.15 g, 1 mmol) and DIPEA (0.21 ml) were dissolved in dry DMF (15 ml) and cooled to 0° C. DCC (0.25 g, 1.2 mmol) was dissolved in DMF (3 ml) and added dropwise to the reaction mixture. The mixture was stirred at room temperature overnight. DCU was filtered off and solvent was removed by vacuum distillation. The remaining solid compound was dissolved in ethyl acetate and washed with NaHCO3(5%), 0.5 N HCl, brine and dried over sodium sulfate. Solvent was removed by rotary evaporator and the compound was purified by column chromatography using 2% methanol in chloroform as eluent afforded 0. 19 g (76%). FAB-MS: M.W. 251 [M+]; NMR assigned.

Workup

additionadded dropwise to the reaction mixture
filtrationDCU was filtered off
customsolvent was removed by vacuum distillation
dissolutionThe remaining solid compound was dissolved in ethyl acetate
washwashed with NaHCO3(5%), 0.5 N HCl, brine
dry with materialdried over sodium sulfate
customSolvent was removed by rotary evaporator
customthe compound was purified by column chromatography
customafforded 0

Sources & evidence

ORD record: ord-1d68d67601ab47df8c71ae25147a856c
Source dataset: uspto-grants-2001_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06288221B1

Reaction notes

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