Dicyclohexylcarbodiimide → HCID 60208933, compound

HRID 1761125Notes

Reaction equation

HRID 1761125 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH3:11])=[C:3]1[CH2:12][NH:13][CH3:14].[NH2:15][C:16]1[N:21]=[CH:20][C:19](/[CH:22]=[CH:23]/[C:24]([OH:26])=O)=[CH:18][CH:17]=1.C1C=CC2N(O)N=NC=2C=1.O.C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl.CN(C=O)C>[NH2:15][C:16]1[N:21]=[CH:20][C:19](/[CH:22]=[CH:23]/[C:24]([N:13]([CH2:12][C:3]2[N:2]([CH3:1])[C:10]3[C:5]([C:4]=2[CH3:11])=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH3:14])=[O:26])=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 27960291-Hydroxybenzotriazole hydrateHCID 10487224(2E)-3-(6-aminopyridin-3-yl)prop-2-enoic acidHCID 22139131(1,3-dimethyl-1H-indol-2-yl)-N-methylmethanamine

Product 1

HCID 60208933HCID 60208933, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1,3-dimethyl-2-(methylaminomethyl)-1H-indole (0.6 g, 3.2 mmole) in 1:1 DMF(CH2Cl2 (25 mL) was added (E)-3-(6aminopyridin-3-yl)acrylicacid (0.50 g, 3 mmole), HOBt H2O (0.43 g, 3.2 mmole), and DCC (0.66 g, 3.2 mmole). After stirring at RT for 16 hr the reaction was concentrated under vacuum. Purification by flash chromatography on silica gel (3% methanoUCHCl3) gave the title compound (0.83 g, 83%) as an off-white solid: LCMS (ES) n/e 335.4 (M+H)+.

Workup

  1. concentrationwas concentrated under vacuum
  2. customPurification by flash chromatography on silica gel (3% methanoUCHCl3)

Sources & evidence

ORD record
ord-f7c554e11e2c46b8a6591004c4124f03
Source dataset
uspto-grants-2005_01
Patent number
US06846819B1

Reaction notes

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