Water → HCID 60208933, compound

HRID 225935Notes

Reaction equation

HRID 225935 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].[C:15]([OH:19])(=O)[CH:16]=[CH2:17].C1C=CC2N(O)N=NC=2C=1.O.[CH2:31]1CC[CH:34]([N:37]=[C:38]=[N:39]C2CCCCC2)[CH2:33][CH2:32]1>CN(C=O)C.C(Cl)Cl>[NH2:39][C:38]1[N:37]=[CH:34][C:33](/[CH:17]=[CH:16]/[C:15]([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:19])=[CH:32][CH:31]=1

Participants

7

Reactant 5

HCID 962WaterHCID 6581Acrylic AcidHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 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-6f12dac6472d44598a0d3090f727dc48
Source dataset
uspto-grants-2009_07
Patent number
US07557125B2

Reaction notes

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