Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 70098057, compound

HRID 2183502Notes

Reaction equation

HRID 2183502 reaction equation
CC([Si](C)(C)[O:6][CH2:7][CH2:8][N:9]1[C:13]([CH2:14][O:15][C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19]3=[N:26][N:27]=[C:28]([C:29]4[CH:33]=[C:32]([CH3:34])[O:31][N:30]=4)[N:18]3[N:17]=2)=[CH:12][N:11]=[N:10]1)(C)C.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>CCO>[CH3:34][C:32]1[O:31][N:30]=[C:29]([C:28]2[N:18]3[N:17]=[C:16]([O:15][CH2:14][C:13]4[N:9]([CH2:8][CH2:7][OH:6])[N:10]=[N:11][CH:12]=4)[C:25]4[C:20]([C:19]3=[N:26][N:27]=2)=[CH:21][CH:22]=[CH:23][CH:24]=4)[CH:33]=1

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 131724936HCID 131724936, compound

Product 1

HCID 70098057HCID 70098057, compoundYield 91.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 6-({[1-(2-{[(dimethylethyl)(dimethyl)silyl]oxy}ethyl)-1H-[1,2,3]triazol-5-yl]methyl}oxy)-3-(5-methylisoxazol-3-yl)-[1,2,4]triazolo[3,4-α]phthalazine (606 mg, 1.2 mmol) and pyridinium para-toluenesulfonate (602 mg, 2.4 mmol) in EtOH (100 ml) was heated at 70° C. for 36 h. The reaction was cooled to room temperature and concentrated to approximately 25 ml, the resulting solid was filtered off and dried to yield the desired phthalazine (429 mg, 91%). 1H NMR (360 MHz, d6-DMSO) δ 8.55 (1H, d, J=8.0 Hz), 8.22 (1H, d, J=8.0 Hz), 8.12-8.00 (2H, m), 7.93 (1H, t, J=8.0 Hz), 7.11 (1H, s), 5.83 (2H, s), 4.58 (2H, t, J=5.3 Hz), 3.84 (2H, t, J=5.3 Hz), 2.59 (3H, s).

Workup

  1. concentrationconcentrated to approximately 25 ml
  2. filtrationthe resulting solid was filtered off
  3. customdried

Sources & evidence

ORD record
ord-7f98ac4c9cc64849980afdedd36fcdf8
Source dataset
uspto-grants-2005_05
Patent number
US06900209B2

Reaction notes

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