Triethylamine → HCID 67540133, compound

HRID 1192417Notes

Reaction equation

HRID 1192417 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[C:17]([O:21][C:22](=[O:35])[NH:23][CH2:24][CH2:25][NH:26][CH2:27][C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=1)([CH3:20])([CH3:19])[CH3:18].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.C(N(CC)CC)C>CN(C=O)C>[C:17]([O:21][C:22](=[O:35])[NH:23][CH2:24][CH2:25][N:26]([CH2:27][C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=1)[C:12](=[O:14])[C:11]1[CH:10]=[CH:9][C:8]([C:5]2[CH:4]=[CH:3][N:2]=[CH:7][CH:6]=2)=[CH:16][CH:15]=1)([CH3:20])([CH3:18])[CH3:19]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 574326074-(Pyridin-4-yl)benzoic acid hydrochlorideHCID 67134877tert-Butyl (2-((4-chlorobenzyl)amino)ethyl)carbamate

Product 1

HCID 67540133HCID 67540133, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The 4-pyridin-4-yl-benzoic acid hydrochloride salt (100 mg, 0.502 mmol), [2-(4-chlorobenzylamino)-ethyl]-carbamic acid tert-butyl ester (143 mg, 0.502 mmol), HOBt (77 mg, 0.502 mmol), and EDCI (56 mg, 0.552 mmol) were dissolved in 1.7 mL DMF, then treated with triethyl amine (77 μL, 0.552 mmol) to room temperature. The reaction was allowed to stir overnight to completion and partitioned between ethyl acetate and diluted NaHCO3 solution. The aqueous was extracted with ethyl acetate, and the organics were combined. The organic was washed with water, brine, dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by chromatography (silica gel eluted with hexanes/ethyl acetate gradients plus 2% triethylamine) to afford the {2-[(4-chlorobenzyl)-(4-pyridin-4-yl-benzoyl)-amino]-ethyl}-carbamic acid tert-butyl ester as a colorless oil (184 mg, 93%). 1H NMR (CDCl3, 400 MHz) δ 8.68 (d, J=4.8 Hz, 2H), 7.65 (m, 2H), 7.54 (d, J=8.4 Hz, 2H), 7.48 (d, J=4.4 Hz, 2H), 7.34 (m, 2H), 7.13 (m, 2H), 4.91 (m, 1H), 4.59 (brs, 2H), 3.62 (m, 2H), 3.44 (m, 2H), 1.46 (s, 9H). LCMS (APCI+) m/z 466 [M+H]+; Rt=3.19 min.

Workup

  1. custompartitioned between ethyl acetate and diluted NaHCO3 solution
  2. extractionThe aqueous was extracted with ethyl acetate
  3. washThe organic was washed with water, brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by chromatography (silica gel eluted with hexanes/ethyl acetate gradients plus 2% triethylamine)

Sources & evidence

ORD record
ord-9db290df3bfa42b2802011c13ec9e1fb
Source dataset
uspto-grants-2014_03
Patent number
US08680114B2

Reaction notes

Loading…