Triethylamine → HCID 67165955, compound

HRID 877373Notes

Reaction equation

HRID 877373 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([OH:13])=O)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[Cl-].[C:15]([CH:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[NH3+:18])#[N:16].Cl.CN(C)CCCN=C=NCC.ON1C2N=CC=CC=2N=N1.C(N(CC)CC)C>O.C(Cl)Cl>[C:15]([CH:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[NH:18][C:11](=[O:13])[CH2:10][C:7]1[CH:6]=[CH:5][C:4]([CH:1]([CH3:2])[CH3:3])=[CH:9][CH:8]=1)#[N:16]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 4083753641-60-4HCID 782304-Isopropylphenylacetic acidHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 67165955HCID 67165955, compoundYield 54.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a 100 ml round bottom flask equipped with a magnetic stir bar were added 4-isopropylphenylacetic acid (1.786 g, 10.02 mmol), cyano(phenyl)-methanaminium chloride (1.690 g, 10.02 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.921 g, 10.02 mmol), 1-hydroxy-7-azabenzotriazole (1.364 g, 10.02 mmol) and triethylamine (3.042 ml, 30.06 mmol) into 30.0 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 preparative HPLC (20-90% CH3CN/H2O over 30 min, 0.05% added TFA, C18 column) to afford 1.6 g (54%) of the title compound. 1H NMR (CDCl3, 400 MHz) δ 7.382 (m, 5H), 7.206 (m, 4H), 6.156 (d, J=8.6 Hz, 1H), 5.997 (br d, J=8.2 Hz, 1H), 3.632 (s, 2H), 2.895 (sept, J=7.0 Hz, 1H), 1.238 (d, J=7.0 Hz, 6H). ES-MS [M+1]+: 293.2.

Workup

  1. customTo a 100 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
  9. additionby preparative HPLC (20-90% CH3CN/H2O over 30 min, 0.05% added TFA, C18 column)

Sources & evidence

ORD record
ord-5466ea500c90474dae7bb2bb9e1f4a32
Source dataset
uspto-grants-2015_03
Patent number
US08987310B2

Reaction notes

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