Taurine → HCID 22502300, compound

HRID 1633977Notes

Reaction equation

HRID 1633977 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]([NH:21][C:22]([NH:24][C:25]2[CH:30]=[CH:29][C:28]([CH3:31])=[C:27]([S:32]([CH3:35])(=[O:34])=[O:33])[CH:26]=2)=[O:23])[C:12]2[CH:20]=[CH:19][C:15]([C:16](O)=[O:17])=[CH:14][CH:13]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].OC1C2N=NNC=2C=CC=1.Cl.CN(C)CCCN=C=NCC.[NH2:58][CH2:59][CH2:60][S:61]([OH:64])(=[O:63])=[O:62].C(N(C(C)C)CC)(C)C.S([O-])(O)(=O)=O.[Na+]>CN(C=O)C.O>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]([NH:21][C:22]([NH:24][C:25]2[CH:30]=[CH:29][C:28]([CH3:31])=[C:27]([S:32]([CH3:35])(=[O:33])=[O:34])[CH:26]=2)=[O:23])[C:12]2[CH:20]=[CH:19][C:15]([C:16]([NH:58][CH2:59][CH2:60][S:61]([OH:64])(=[O:63])=[O:62])=[O:17])=[CH:14][CH:13]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

9

Reactant 6

HCID 1123TaurineHCID 81531DiisopropylethylamineHCID 516919Sodium BisulfateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22501902HCID 22501902, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 22502300HCID 22502300, compoundYield 55.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

4-[1-(4-tert-Butylphenyl)-3-(3-methylsulfonyl-4-methylphenyl)ureidomethyl]benzoic acid (300 mg, 0.6 mmol) was dissolved in DMF (10 ml). Hydroxybenzotriazole (100 mg, 0.7 mmol), and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (130 mg, 0.7 mmol) were added and the mixture was stirred for 30 minutes at room temperature followed by addition of 2-aminoethanesulfonic acid (110 mg, 0.9 mmol) and diisopropylethylamine (120 mg, 160 μl, 1.0 mmol). After 16 hours the reaction mixture was poured into water (40 mL), pH was adjusted to acidic reaction with sodium hydrogen sulphate and the solution was concentrated in vacuo. The residue was purified by flash chromatography (20 g Silica Gel) using methanol and dichloromethane (10:90) as eluent to give 0.2 g of the title compound.

Workup

  1. concentrationthe solution was concentrated in vacuo
  2. customThe residue was purified by flash chromatography (20 g Silica Gel)

Sources & evidence

ORD record
ord-540abc80ec25480a89b44399fe5d25e4
Source dataset
uspto-grants-2003_01
Patent number
US06503949B1

Reaction notes

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