2-Pyridinemethanamine → HCID 69587996, compound

HRID 1794288Notes

Reaction equation

HRID 1794288 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][N:7]3[C:13]([C:14]4[C:15]([C:20]5[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=5)=[N:16][O:17][C:18]=4Cl)=[N:12][N:11]=[C:8]32)=[CH:4][CH:3]=1.C([O-])(=O)C.[Na+].[NH2:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=1>CO>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][N:7]3[C:13]([C:14]4[C:15]([C:20]5[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=5)=[N:16][O:17][C:18]=4[C:38]4[C:33]([CH2:32][NH2:31])=[N:34][CH:35]=[CH:36][CH:37]=4)=[N:12][N:11]=[C:8]32)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 195092-PyridinemethanamineHCID 517045Sodium AcetateHCID 22220922HCID 22220922, compound

Product 1

HCID 69587996HCID 69587996, compoundYield 18.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

8-Bromo-3-(5-chloro-3-phenylisoxazol-4-yl)-5H-[1,2,4]triazolo[3,4-a]isoindole (50 mg, 0.12 mmol) (prepared in Example 39), sodium acetate (30 mg) and 2-(aminomethyl)pyridine (13 mg) in 5 ml methanol were heated to reflux for 18 h. The reaction was cooled, concentrated and partitioned between H2O—CH2Cl2. The organic phase and extracts were combined, dried over (MgSO4) and concentrated. The residue was purified by preparative TLC using 3% MeOH—CH2Cl2 as eluent. Trituration with 1PrOH gave the title compound as a beige solid (11 mg). 1H NMR (400 MHz, d6-DMSO) δ 8.53–8.54 (1H, m), 8.38–8.40 (1H, m), 8.1 (1H, s), 7.75–7.8 (1H, m), 7.65–7.68 (1H, m), 7.55–7.60 (2H, m), 7.38–7.5 (4H, m), 7.28–7.30 (2H, m), 4.68–4.7 (2H, m), 4.45 (2H, s). m/z (ES+) 485/487 (M+H)+.

Workup

  1. temperatureto reflux for 18 h
  2. temperatureThe reaction was cooled
  3. concentrationconcentrated
  4. custompartitioned between H2O—CH2Cl2
  5. dry with materialdried over (MgSO4)
  6. concentrationconcentrated
  7. customThe residue was purified by preparative TLC

Sources & evidence

ORD record
ord-57fd2ef4410d4078bc166a9ddacf6023
Source dataset
uspto-grants-2006_04
Patent number
US07022724B2

Reaction notes

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