1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → N-[4-methyl-3-(pyrimidin-5-yl)-phenyl]-3-methyl-2-trifluoromethyl-1H-indole-7-carboxamide

HRID 1835464Notes

Reaction equation

HRID 1835464 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[NH:4][C:5]2[C:10]([C:11]=1[CH3:12])=[CH:9][CH:8]=[CH:7][C:6]=2[C:13]([OH:15])=O.[CH3:18][C:19]1[CH:25]=[CH:24][C:22]([NH2:23])=[CH:21][C:20]=1[C:26]1[CH:27]=[N:28][CH:29]=[N:30][CH:31]=1.Cl.C(N=C=NCCCN(C)C)C>ClCCl.CN(C)C1C=CN=CC=1>[CH3:18][C:19]1[CH:25]=[CH:24][C:22]([NH:23][C:13]([C:6]2[CH:7]=[CH:8][CH:9]=[C:10]3[C:5]=2[NH:4][C:3]([C:2]([F:1])([F:17])[F:16])=[C:11]3[CH3:12])=[O:15])=[CH:21][C:20]=1[C:26]1[CH:31]=[N:30][CH:29]=[N:28][CH:27]=1

Participants

6

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 235036604-Methyl-3-(pyrimidin-5-yl)anilineHCID 235036882-Trifluoromethyl-3-methylindole-7-carboxylic acid

Product 1

HCID 23503649N-[4-methyl-3-(pyrimidin-5-yl)-phenyl]-3-methyl-2-trifluoromethyl-1H-indole-7-carboxamideYield 75.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 2-trifluoromethyl-3-methylindole-7-carboxylic acid (122 mg) and 4-methyl-3-(pyrimidin-5-yl)aniline (93 mg) in dichloromethane (5 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 24 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 2% methanol in dichloromethane to give N-[4-methyl-3-(pyrimidin-5-yl)-phenyl]-3-methyl-2-trifluoromethyl-1H-indole-7-carboxamide (155 mg, 75.6%).

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 2% methanol in dichloromethane

Sources & evidence

ORD record
ord-62c7e2c9b4734f8f979b6935316d82f7
Source dataset
uspto-grants-2004_08
Patent number
US06770667B1

Reaction notes

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