Aniline → HCID 57611859, compound

HRID 1919918Notes

Reaction equation

HRID 1919918 reaction equation
[C:1]([O:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([CH:14]([CH2:18][N:19]([CH3:21])[CH3:20])[C:15]([O-:17])=O)=[CH:10][CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[K+].CCN=C=NCCCN(C)C.[CH:34]1[CH:35]=[CH:36][C:37]2N(O)N=[N:40][C:38]=2[CH:39]=1.NC1C=CC=CC=1>CN(C=O)C>[NH:40]([C:15](=[O:17])[CH:14]([C:11]1[CH:10]=[CH:9][C:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])=[CH:13][CH:12]=1)[CH2:18][N:19]([CH3:21])[CH3:20])[C:38]1[CH:39]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

6

Reactant 4

HCID 6115AnilineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide2×HCID 757711-HydroxybenzotriazoleHCID 67497698HCID 67497698, compound

Product 1

HCID 57611859HCID 57611859, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Crude potassium 2-[4-(tert-butoxycarbonyl)phenyl]-3-(dimethylamino)propanoate (925 mg, ˜2.79 mmol), EDCI (803 mg, 4.19 mmol), and HOBT (491 mg, 3.63 mg) were combined in DMF (15 mL) and stirred for 5 minutes before adding aniline (331 μL, 3.63 mmol). The reaction was stirred at room temperature for 3 h. Additional EDCI (200 mg) was added, and the reaction was stirred for another 3 h. The mixture was concentrated and purified by reverse phase HPLC (50-95% MeCN/water). The resulting residue was dissolved in EtOAc, neutralized with sat. NaHCO3, washed with brine, dried (MgSO4), and concentrated to give tert-butyl 4-{2-anilino-1-[(dimethylamino)methyl]-2-oxoethyl}benzoate as a white solid. 1H NMR (CDCl3) δ 7.97 (d, J=8.5 Hz, 2H), 7.33 (d, J=8.5 Hz, 2H), 7.21 (dd, J=8.5, 7.3 Hz, 2H), 6.77 (t, J=7.3 Hz, 1H), 6.72 (d, J=7.9 Hz, 2H), 4.22 (dd, J=8.8, 5.0 Hz, 1H), 3.80 (dd, J=13.8, 9.1 Hz, 1H), 3.40 (dd, J=13.6, 4.8 Hz, 1H), 2.95 (s, 3H), 2.74 (s, 3H), 1.58 (s, 9H). MS (ESI) calcd [M+H]+ 369.2, found 369.2.

Workup

  1. stirringThe reaction was stirred at room temperature for 3 h
  2. stirringthe reaction was stirred for another 3 h
  3. concentrationThe mixture was concentrated
  4. custompurified by reverse phase HPLC (50-95% MeCN/water)
  5. dissolutionThe resulting residue was dissolved in EtOAc
  6. washwashed with brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-9c498e0f7333403cb2907359b7c00798
Source dataset
uspto-grants-2012_05
Patent number
US08168658B2

Reaction notes

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