Ammonium Chloride → ethyl 3-{[(4-{[1-(5-chloro-1-methyl-1H-indol-2-yl)heptyl]amino}phenyl)carbonyl](methyl)amino}propanoate

HRID 2091306Notes

Reaction equation

HRID 2091306 reaction equation
Cl[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)N(C)[C:6]([CH:12]([NH:19][C:20]1[CH:28]=[CH:27][C:23]([C:24](O)=O)=[CH:22][CH:21]=1)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[CH:5]2.[CH3:29][NH:30][CH2:31][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34].[OH2:38].ON1C2C=CC=C[C:43]=2N=N1.[ClH:49].C(N=C=NCCCN(C)C)C.[Cl-].[NH4+:62]>CN(C)C=O.C(N(CC)CC)C>[Cl:49][C:9]1[CH:8]=[C:4]2[C:3](=[CH:2][CH:10]=1)[N:62]([CH3:43])[C:6]([CH:12]([NH:19][C:20]1[CH:21]=[CH:22][C:23]([C:24]([N:30]([CH3:29])[CH2:31][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])=[O:38])=[CH:27][CH:28]=1)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[CH:5]2

Participants

8

Reactant 5

HCID 25517Ammonium ChlorideHCID 541480Ethyl 3-(methylamino)propanoateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 667778124-{[1-(5-chloro-1-methyl-1H-indol-2-yl)heptyl]amino}benzoic acid

Product 1

HCID 68627241ethyl 3-{[(4-{[1-(5-chloro-1-methyl-1H-indol-2-yl)heptyl]amino}phenyl)carbonyl](methyl)amino}propanoateYield 61%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a mixture of 4-{[1-(5-chloro-1-methyl-1H-indol-2-yl)heptyl]amino}benzoic acid (300 mg) synthesized in Example A140(3), ethyl 3-(methylamino)propanoate (148 mg), 1-hydroxybenzotriazole monohydrate (173 mg), triethylamine (158 μL) and N,N-dimethylformamide (10 mL) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (217 mg), and the mixture was stirred overnight at room temperature. Saturated aqueous ammonium chloride solution was added to quench the reaction, and the reaction mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (30-70% ethyl acetate/hexane) to give the title object compound (235 mg, 61%) as a pale-yellow oil.

Workup

  1. customto quench
  2. customthe reaction
  3. extractionthe reaction mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (30-70% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-db03a782759a452c80e197a5eec84184
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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