Triethylamine → HCID 178491178, compound

HRID 877388Notes

Reaction equation

HRID 877388 reaction equation
[Cl-].[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]([C:12]2[N:13]=[C:14]([CH3:17])[NH:15][CH:16]=2)[NH3+:11])=[CH:6][CH:5]=1.[CH:18]1([C:21]2[CH:26]=[CH:25][C:24]([CH2:27][C:28](O)=[O:29])=[CH:23][CH:22]=2)[CH2:20][CH2:19]1.Cl.CN(C)CCCN=C=NCC.ON1C2N=CC=CC=2N=N1.C(N(CC)CC)C>O.C(Cl)Cl>[CH:18]1([C:21]2[CH:22]=[CH:23][C:24]([CH2:27][C:28]([NH:11][CH:10]([C:7]3[CH:6]=[CH:5][C:4]([O:3][CH3:2])=[CH:9][CH:8]=3)[C:12]3[N:13]=[C:14]([CH3:17])[NH:15][CH:16]=3)=[O:29])=[CH:25][CH:26]=2)[CH2:20][CH2:19]1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 204905282-(4-Cyclopropylphenyl)acetic acidHCID 178491234HCID 178491234, compound

Product 1

HCID 178491178HCID 178491178, compoundYield 57.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a 50 ml round bottom flask equipped with a magnetic stir bar were added (4-methoxyphenyl)(2-methyl-1H-imidazol-4-yl)methanaminium chloride (0.350 g, 1.206 mmol), 4-cyclopropylphenylacetic acid (0.213 mg, 1.206 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.231 g, 1.206 mmol), 1-hydroxy-7-azabenzotriazole (0.164 mg, 1.206 mmol) and triethylamine (0.336 ml, 2.412 mmol) into 10.0 ml of CH2Cl2. The resulting solution was stirred at room temperature for 16 hours. The reaction mixture was diluted with water and the two layers were separated. The aqueous layer was extracted with CH2Cl2. The combined organic layers were washed with brine, dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated in vacuum. Purification by flash chromatography (SiO2, 0-10% methanol in CH2Cl2, gradient) gave the title compound as a white solid (0.260 g, 57%). 1H NMR (CDCl3, 400 MHz) δ 7.151 (m, 4H), 7.021 (d, J=8.24 Hz, 2H), 7.820 (d, J=8.60 Hz, 2H), 6.459 (s, 1H), 6.459 (br s, 1H), 5.989 (d, J=7.32 Hz, 1H), 3.778 (s, 3H), 3.552 (s, 2H), 2.355 (s, 3H), 1.870 (m, 1H), 0.950 (m, 2H), 0.669 (m, 2H). ES-MS [M+1]+: 376.3.

Workup

  1. customTo a 50 ml round bottom flask equipped with a magnetic stir bar
  2. customthe two layers were separated
  3. extractionThe aqueous layer was extracted with CH2Cl2
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated in vacuum
  8. customPurification by flash chromatography (SiO2, 0-10% methanol in CH2Cl2, gradient)

Sources & evidence

ORD record
ord-6e4b88f52e5e49f7bf9af856a996d8e2
Source dataset
uspto-grants-2015_03
Patent number
US08987310B2

Reaction notes

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