1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → Carbonate tert-butyl [2-({4-[2-anilino-1-(anilinocarbonyl)-2-oxoethyl]benzoyl}amino)phenyl]carbamate

HRID 1694838Notes

Reaction equation

HRID 1694838 reaction equation
[NH:1]([C:8](=[O:28])[CH:9]([C:19]1[CH:27]=[CH:26][C:22]([C:23]([OH:25])=[O:24])=[CH:21][CH:20]=1)[C:10]([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN=C=NCCCN(C)C.C1C=CC2N([OH:49])N=NC=2C=1.[NH2:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][C:52]=1[NH:57][C:58](=[O:64])[O:59][C:60]([CH3:63])([CH3:62])[CH3:61]>CN(C=O)C>[NH:1]([C:8](=[O:28])[CH:9]([C:19]1[CH:20]=[CH:21][C:22]([C:23]([NH:50][C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][C:52]=2[NH:57][C:58](=[O:64])[O:59][C:60]([CH3:61])([CH3:63])[CH3:62])=[O:24])=[CH:26][CH:27]=1)[C:10]([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:23](=[O:24])([OH:49])[OH:25]

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 676311N-(tert-Butoxycarbonyl)-1,2-phenylenediamineHCID 593764614-[2-Anilino-1-(anilinocarbonyl)-2-oxoethyl]benzoic acid

Product 1

HCID 131729634Carbonate tert-butyl [2-({4-[2-anilino-1-(anilinocarbonyl)-2-oxoethyl]benzoyl}amino)phenyl]carbamateYield 115.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-[2-anilino-1-(anilinocarbonyl)-2-oxoethyl]benzoic acid (110 mg, 0.29 mmol) in DMF (2 mL) at room temperature was added EDCI (67 mg, 0.35 mmol) and HOBT (48 mg, 0.36 mmol). The solution was stirred for 30 min and tert-butyl (2-aminophenyl)carbamate (85 mg, 0.41 mmol) was added in one portion. The reaction mixture was stirred at room temperature for 20 h and purified by reverse phase HPLC (30% to 95% MeCN in water) to give carbonate tert-butyl [2-({4-[2-anilino-1-(anilinocarbonyl)-2-oxoethyl]benzoyl}amino)phenyl]carbamate (105 mg, 64%) as a white solid: 1H NMR (600 MHz, DMSO-d6) δ 10.27 (s br, 2H), 9.83 (s br, 1H), 8.64 (s br, 1H), 7.94 (d, J=8.2 Hz, 2H), 7.60-7.58 (m, 6H), 7.53 (t, J=8.8 Hz, 2H), 7.31 (t, J=8.1 Hz, 41-1), 7.19 (td, J=7.6, 1.5 Hz, 1H), 7.13 (td, J=7.6, 1.5 Hz, 1H), 7.06 (t, J=7.3 Hz, 2H), 4.98 (s, 1H), 1.42 (s, 9H); ESIMS calcd 587.2 (M++Na), found 587.2 (M++Na).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 20 h
  2. custompurified by reverse phase HPLC (30% to 95% MeCN in water)

Sources & evidence

ORD record
ord-15ded420d6ba43e39bcff01528d27e4a
Source dataset
uspto-grants-2012_04
Patent number
US08158825B2

Reaction notes

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