Triethylamine → HCID 57224276, compound

HRID 1635039Notes

Reaction equation

HRID 1635039 reaction equation
C(N(CC)CC)C.Cl.C(N=C=NCCCN(C)C)C.[F:20][C:21]1[CH:22]=[C:23]2[C:27](=[CH:28][CH:29]=1)[NH:26][CH:25]=[C:24]2[CH:30]1[CH2:35][CH2:34][CH:33]([C:36]([OH:38])=O)[CH2:32][CH2:31]1.[CH3:39][O:40][C:41]1[CH:47]=[CH:46][C:44]([NH2:45])=[CH:43][C:42]=1[N:48]1[CH2:53][CH2:52][N:51]([CH3:54])[CH2:50][CH2:49]1>ClCCl>[CH3:39][O:40][C:41]1[CH:47]=[CH:46][C:44]([NH:45][C:36]([CH:33]2[CH2:32][CH2:31][CH:30]([C:24]3[C:23]4[C:27](=[CH:28][CH:29]=[C:21]([F:20])[CH:22]=4)[NH:26][CH:25]=3)[CH2:35][CH2:34]2)=[O:38])=[CH:43][C:42]=1[N:48]1[CH2:49][CH2:50][N:51]([CH3:54])[CH2:52][CH2:53]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 103311014-Methoxy-3-(4-methylpiperazin-1-yl)anilineHCID 18675596HCID 18675596, compound

Product 1

HCID 57224276HCID 57224276, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

173 μl (1.2 mmol) of triethylamine and 230 mg (1.2 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride are added to a mixture of 314 mg (1.2 mmol) of 4-(5-fluoro-1H-indol-3-yl)cyclo-hexanecarboxylic acid and 265 mg (1.2 mmol) of 4-methoxy-3-(4-methylpiperazin-1-yl)aniline in 40 ml of dichloromethane. This mixture is initially stirred at 0° for one hour, then at room temperature for 12 h. The reaction mixture is concentrated, the residue is taken up in ethyl acetate, and the mixture is washed with water, 5% citric acid and sat. sodium bicarbonate solution, dried and evaporated. After column chromatographic separation, 4-(5-fluoro-1H-indol-3-yl)-cyclohexanoic acid [4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]amide is obtained.

Workup

  1. waitat room temperature for 12 h
  2. concentrationThe reaction mixture is concentrated
  3. washthe mixture is washed with water, 5% citric acid and sat. sodium bicarbonate solution
  4. customdried
  5. customevaporated
  6. customAfter column chromatographic separation

Sources & evidence

ORD record
ord-bdf70206a3e6444f924db4700f6e8aae
Source dataset
uspto-grants-2003_01
Patent number
US06509340B1

Reaction notes

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