p-Toluenesulfonic acid → HCID 59344704, compound

HRID 17999Notes

Reaction equation

HRID 17999 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-932e34f7097c46638864a3a6e69ec2c1
Source dataset
uspto-grants-2010_06
Patent number
US07741315B2

Reaction notes

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