Pyridine → HCID 68904285, compound

HRID 490053Notes

Reaction equation

HRID 490053 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]2[S:10][C:9](=[O:11])[N:8]([CH:12]3[O:20][CH:19]4[CH:14]([O:15][Si](C(C)(C)C)(C(C)(C)C)[O:17][CH2:18]4)[CH:13]3[O:29][C:30](=[O:32])[CH3:31])[C:6]=2[N:7]=1.N1C=CC=CC=1>CO>[NH2:1][C:2]1[N:3]=[CH:4][C:5]2[S:10][C:9](=[O:11])[N:8]([CH:12]3[CH:13]([O:29][C:30](=[O:32])[CH3:31])[CH:14]([OH:15])[CH:19]([CH2:18][OH:17])[O:20]3)[C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 1049PyridineHCID 68905530HCID 68905530, compound

Product 1

HCID 68904285HCID 68904285, compoundYield 90.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 17 (2.28 g, 4.73 mmol) in 10 mL anhydrous methanol was added 327 μL HF/Pyridine. The reaction was stirred at room temperature for 1 hour. The mixture was concentrated and purified by flash chromatography (0-10% MeOH—CH2Cl2) yielding 1.47 g (90%) 18: 1H NMR (400 MHz, DMSO-d6) δ 8.38 (1H, s), 6.86 (2H, bs), 5.82 (1H, d, J=4.68 Hz), 5.76-5.78 (1H, m), 5.34 (1H, d, J=7.8 Hz), 4.60 (1H, t, J=5.46 Hz), 4.27-4.31 (1H, m), 3.96-4.00 (1H, m), 3.61-3.72 (2H, m), 2.03 (3H, s); [M]+ @ m/z 343.3.

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by flash chromatography (0-10% MeOH—CH2Cl2)

Sources & evidence

ORD record
ord-8cfb0ce115814a66a0532c603b1d1483
Source dataset
uspto-grants-2009_05
Patent number
US07528115B2

Reaction notes

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