1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → N-[3-(1,2-dimethyl-1H-imidazol-5-yl)-phenyl]-2,3-dimethyl-1H-indole-7-carboxamide

HRID 1835457Notes

Reaction equation

HRID 1835457 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH3:11])=[CH:8][CH:7]=[CH:6][C:5]=2[C:12]([OH:14])=O.[CH3:15][N:16]1[C:20]([C:21]2[CH:22]=[C:23]([CH:25]=[CH:26][CH:27]=2)[NH2:24])=[CH:19][N:18]=[C:17]1[CH3:28].Cl.C(N=C=NCCCN(C)C)C>ClCCl.CN(C)C1C=CN=CC=1>[CH3:15][N:16]1[C:20]([C:21]2[CH:22]=[C:23]([NH:24][C:12]([C:5]3[CH:6]=[CH:7][CH:8]=[C:9]4[C:4]=3[NH:3][C:2]([CH3:1])=[C:10]4[CH3:11])=[O:14])[CH:25]=[CH:26][CH:27]=2)=[CH:19][N:18]=[C:17]1[CH3:28]

Participants

6

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 37026102,3-Dimethyl-7-indolecarboxylic acidHCID 235036623-(1,2-dimethyl-1H-imidazol-5-yl)aniline

Product 1

HCID 23503674N-[3-(1,2-dimethyl-1H-imidazol-5-yl)-phenyl]-2,3-dimethyl-1H-indole-7-carboxamideYield 40.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 2,3-dimethylindole-7-carboxylic acid (95 mg) and 3-(1,2-dimethylimidazol-5-yl)aniline (94 mg) in dichloromethane (3 ml) were added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (144 mg) and 4-dimethylaminopyridine (30 mg). The mixture was stirred at ambient temperature for 18 hours and diluted with dichloromethane. The solution was washed with water and brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified by a silica gel column chromatography eluting with 3% methanol in dichloromethane to give N-[3-(1,2-dimethyl-1H-imidazol-5-yl)-phenyl]-2,3-dimethyl-lH-indole-7-carboxamide (73 mg, 40.8%).

Workup

  1. washThe solution was washed with water and brine
  2. dry with materialdried over magnesium sulfate
  3. customevaporated under reduced pressure
  4. customThe residue was purified by a silica gel column chromatography
  5. washeluting with 3% methanol in dichloromethane

Sources & evidence

ORD record
ord-572c2885b4c040b79eb4ced5f06acb88
Source dataset
uspto-grants-2004_08
Patent number
US06770667B1

Reaction notes

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