Taurine → 2-(4-{[(4-Benzofuran-2-yl-phenylcarbamoyl)-(4-tert-butyl-phenyl)-methyl]-methyl-amino}-benzoylamino)-ethanesulfonic Acid

HRID 2371269Notes

Reaction equation

HRID 2371269 reaction equation
[O:1]1[C:6]2=[CH:7][CH:8]=[CH:9][C:5]2=[CH:4][CH:3]=[C:2]1[N:10]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:11]([CH:13]([N:24]([CH3:34])[C:25]1[CH:33]=[CH:32][C:28]([C:29](O)=[O:30])=[CH:27][CH:26]=1)[C:14]1[CH:19]=[CH:18][C:17]([C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:16][CH:15]=1)=[O:12].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[NH2:62][CH2:63][CH2:64][S:65]([OH:68])(=[O:67])=[O:66].CCN(C(C)C)C(C)C>CN(C=O)C>[O:1]1[C:6]2=[CH:7][CH:8]=[CH:9][C:5]2=[CH:4][CH:3]=[C:2]1[N:10]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:11]([CH:13]([N:24]([CH3:34])[C:25]1[CH:26]=[CH:27][C:28]([C:29]([NH:62][CH2:63][CH2:64][S:65]([OH:68])(=[O:67])=[O:66])=[O:30])=[CH:32][CH:33]=1)[C:14]1[CH:15]=[CH:16][C:17]([C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:18][CH:19]=1)=[O:12]

Participants

7

Reactant 5

HCID 1123TaurineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 674860264-{[(4-Benzofuran-2-yl-phenylcarbamoyl)-(4-tert-butyl-phenyl)-methyl]-methyl-amino}-benzoic Acid

Product 1

HCID 866697872-(4-{[(4-Benzofuran-2-yl-phenylcarbamoyl)-(4-tert-butyl-phenyl)-methyl]-methyl-amino}-benzoylamino)-ethanesulfonic AcidYield 94.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-{[(4-Benzofuran-2-yl-phenylcarbamoyl)-(4-tert-butyl-phenyl)-methyl]-methyl-amino}-benzoic acid (110 mg, 0.2 mmol), was taken up in 3 mL of DMF followed by addition of HOBt (79 mg, 0.52 mmol) and EDCI (99 mg, 0.52 mmol). The reaction was stirred at RT for 30 min, taurine (103 mg, 0.083 mmol) was added followed by Hunig's base (107 mg, 0.083 mmol) and allowed to stir an additional 16 h at RT. The solution was filtered through a frit and the DMF was subjected to reverse phase HPLC purification. After removal acetonitrile/water under reduced pressure, followed by trituration with methanol, gave a white solid (50 mg, 39%).

Workup

  1. stirringto stir an additional 16 h at RT
  2. filtrationThe solution was filtered through a frit
  3. customphase HPLC purification
  4. customAfter removal acetonitrile/water under reduced pressure

Sources & evidence

ORD record
ord-0ccd59dfafcd4ec08035bbe8a2c48a1e
Source dataset
uspto-grants-2014_04
Patent number
US08710236B2

Reaction notes

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