Triethylamine → HCID 57964394, compound

HRID 2403543Notes

Reaction equation

HRID 2403543 reaction equation
Cl.[F:2][C:3]([F:29])([F:28])[C:4]1[CH:5]=[C:6]([N:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH:18]3[CH2:23][CH2:22][C:21](=[CH:24][C:25](O)=[O:26])[CH2:20][CH2:19]3)[CH2:12][CH2:11]2)[CH:7]=[CH:8][CH:9]=1.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.C(N(CC)CC)C.Cl.[CH3:60][NH:61][O:62][CH3:63]>ClCCl>[CH3:63][O:62][N:61]([CH3:60])[C:25](=[O:26])[CH:24]=[C:21]1[CH2:22][CH2:23][CH:18]([CH2:17][CH2:16][N:13]2[CH2:12][CH2:11][N:10]([C:6]3[CH:7]=[CH:8][CH:9]=[C:4]([C:3]([F:28])([F:29])[F:2])[CH:5]=3)[CH2:15][CH2:14]2)[CH2:19][CH2:20]1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 131731752HCID 131731752, compound

Product 1

HCID 57964394HCID 57964394, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 200 mg (0.46 mmol) of (4-{2-[4-(3-trifluoromethylphenyl)piperazin-1-yl]ethyl}cyclohexylidene)acetic acid, hydrochloride in 5 mL of dichloromethane stabilized on amylene are successively added 63 mg (0.46 mmol) of 1-hydroxybenzotriazole, 88 mg (0.46 mmol) of 3-ethyl-1-(3-dimethylaminopropyl)carbodiimide hydrochloride and 140 mg (1.4 mmol) of triethylamine. The mixture is stirred for 15 minutes then 45 mg (0.46 mmol) of N,O-dimethylhydroxylamine hydrochloride are added. The mixture is stirred overnight at room temperature, then evaporated under reduced pressure. The residue is dissolved in ethyl acetate and washed twice with water. The organic phase is dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue is purified over 10 g of silica gel (eluant dichloromethane/methanol 98/2) to give 143 mg (71%) of N-methoxy-N-methyl-2-(4-{2-[4-(3-trifluoromethylphenyl)piperazin-1-yl]ethyl}cyclohexylidene)acetamide as an oil.

Workup

  1. stirringThe mixture is stirred overnight at room temperature
  2. customevaporated under reduced pressure
  3. dissolutionThe residue is dissolved in ethyl acetate
  4. washwashed twice with water
  5. dry with materialThe organic phase is dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue is purified over 10 g of silica gel (eluant dichloromethane/methanol 98/2)

Sources & evidence

ORD record
ord-7b171e3bdc344d4a814f521be775633a
Source dataset
uspto-grants-2014_08
Patent number
US08802678B2

Reaction notes

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