Water → HCID 60208933, compound

HRID 2112719Notes

Reaction equation

HRID 2112719 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>CN(C=O)C.C(Cl)Cl>[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 5

HCID 962WaterHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 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 1

HCID 22350042dichloromethane N,N-dimethylformamideSolvent

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-(6-aminopyridin-3-yl)acrylic acid (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% methanol/CHCl3) gave the title compound (0.83 g, 83%) as an off-white solid: LCMS (ES) m/e 335.4 (M+H)+.

Workup

  1. concentrationwas concentrated under vacuum
  2. customPurification by flash chromatography on silica gel (3% methanol/CHCl3)

Sources & evidence

ORD record
ord-2b3ee0a8e04a4af0ae5de977aa853137
Source dataset
uspto-grants-2009_04
Patent number
US07524843B2

Reaction notes

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