p-Toluenesulfonic acid → HCID 56849174, compound

HRID 2040025Notes

Reaction equation

HRID 2040025 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3([C:18]4[N:22]=[C:21]([C:23]5[CH:24]=[N:25][N:26]([CH2:28][C:29]([N:31]6[CH2:35][CH2:34][CH:33]([O:36]C7CCCCO7)[CH2:32]6)=[O:30])[CH:27]=5)[O:20][N:19]=4)[CH2:17][CH2:16][CH2:15]3)=[CH:10][CH:9]=2)=[CH:4][N:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)C>[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3([C:18]4[N:22]=[C:21]([C:23]5[CH:24]=[N:25][N:26]([CH2:28][C:29]([N:31]6[CH2:35][CH2:34][CH:33]([OH:36])[CH2:32]6)=[O:30])[CH:27]=5)[O:20][N:19]=4)[CH2:17][CH2:16][CH2:15]3)=[CH:10][CH:9]=2)=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 68075548HCID 68075548, compound

Product 1

HCID 56849174HCID 56849174, compoundYield 39.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

R105 (65.0 mg, 0.114 mmol) is treated with ethanol (1.5 mL) and p-toluenesulfonic acid (5.7 mg, 0.20 mmol) and the resulting mixture is stirred at 60° C. for 2.5 hours. The reaction was cooled to room temperature and filtered. The resulting solid was purified by reverse-phase preparative HPLC eluting 10-90% acetonitrile/water/0.1% formic acid to give Example 239 (22.0 mg); m/z 487.4 [M+1].

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. filtrationfiltered
  3. customThe resulting solid was purified by reverse-phase preparative HPLC
  4. washeluting 10-90% acetonitrile/water/0.1% formic acid

Sources & evidence

ORD record
ord-1d276106311f4cce845d2731f05118f0
Source dataset
uspto-grants-2013_11
Patent number
US08580829B2

Reaction notes

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