1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → ethyl 5-({[4-(cyclopropylmethoxy)phenyl]carbonyl}amino)-1-methyl-1H-indole-2-carboxylate

HRID 239896Notes

Reaction equation

HRID 239896 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[C:6]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:5]2.[CH:17]1([CH2:20][O:21][C:22]2[CH:30]=[CH:29][C:25]([C:26](O)=[O:27])=[CH:24][CH:23]=2)[CH2:19][CH2:18]1.O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>CN(C=O)C.O.C(OCC)(=O)C>[CH:17]1([CH2:20][O:21][C:22]2[CH:23]=[CH:24][C:25]([C:26]([NH:1][C:2]3[CH:3]=[C:4]4[C:8](=[CH:9][CH:10]=3)[N:7]([CH3:11])[C:6]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:5]4)=[O:27])=[CH:29][CH:30]=2)[CH2:18][CH2:19]1

Participants

8

Reactant 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 11424506Ethyl 5-amino-1-methyl-1H-indole-2-carboxylateHCID 226453014-(Cyclopropylmethoxy)benzoic acid

Product 1

HCID 70967959ethyl 5-({[4-(cyclopropylmethoxy)phenyl]carbonyl}amino)-1-methyl-1H-indole-2-carboxylateYield 64%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of ethyl 5-amino-1-methyl-1H-indole-2-carboxylate (2.293 g) and 4-(cyclopropylmethoxy)benzoic acid (1.897 g) in DMF (23 mL) were added 1-hydroxybenzotriazole monohydrate (1.965 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (2.460 g) and N,N-dimethylaminopyridine (1.326 g), and the mixture was stirred at room temperature for 17 hr. After dilution with ethyl acetate, water was added, and the organic layer was washed successively with 1N hydrochloric acid, 1N aqueous, sodium hydroxide solution and saturated brine, and concentrated under reduced pressure. The residue was suspended in ethyl acetate, and the precipitate was collected by filtration, washed with ethyl acetate, and dried under reduced pressure to give the title compound (2.466 g, yield 64%) as a beige solid.

Workup

  1. washthe organic layer was washed successively with 1N hydrochloric acid, 1N aqueous
  2. concentrationsodium hydroxide solution and saturated brine, and concentrated under reduced pressure
  3. filtrationthe precipitate was collected by filtration
  4. washwashed with ethyl acetate
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-673f5a2c6431435893e80711a3a1d2fa
Source dataset
uspto-grants-2014_02
Patent number
US08642770B2

Reaction notes

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