p-Toluenesulfonic acid → HCID 59344704, compound

HRID 2066581Notes

Reaction equation

HRID 2066581 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:34]=[CH:35][C:36]=1[F:37])[CH2:5][N:6]1[CH2:15][CH2:14][C:13]2[C:8](=[C:9]([OH:32])[C:10](=[O:31])[N:11]3[CH2:20][CH2:19][CH2:18][N:17](CC4C=CC(OC)=CC=4)[C:16](=[O:30])[C:12]3=2)[C:7]1=[O:33].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:34]=[CH:35][C:36]=1[F:37])[CH2:5][N:6]1[CH2:15][CH2:14][C:13]2[C:8](=[C:9]([OH:32])[C:10](=[O:31])[N:11]3[CH2:20][CH2:19][CH2:18][NH:17][C:16](=[O:30])[C:12]3=2)[C:7]1=[O:33]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 66996884HCID 66996884, compound

Product 1

HCID 59344704HCID 59344704, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 10-(3-chloro-4-fluorobenzyl)-8-hydroxy-2-(4-methoxybenzyl)-2,3,4,5,11,12-hexahydro[1,4]diazepino[2,1-a]-2,6-naphthyridine-1,7,9(10H)-trione (18 mg, 30 μmol) and p-toluenesulfonic acid (26 mg, 0.14 mmol) in toluene (0.5 mL) was heated at 110° C. for 8 hours. The reaction mixture was concentrated under vacuum. The residue was purified by reverse phase high pressure liquid chromatography. Collection and lyophilization of appropriate fractions provided the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. customThe residue was purified by reverse phase high pressure liquid chromatography
  3. customCollection and lyophilization of appropriate fractions

Sources & evidence

ORD record
ord-136a7f34870c4094822b40b90b26f569
Source dataset
uspto-grants-2012_10
Patent number
US08293731B2

Reaction notes

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