Azobisisobutyronitrile → HCID 21081533, compound

HRID 347525Notes

Reaction equation

HRID 347525 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][N:5]2[C:10]=1[C:9]([S:11][CH3:12])=[N:8][CH:7]=[N:6]2.C1C(=O)N(Br)C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C.[OH:33][CH:34]1[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]1.CCN(C(C)C)C(C)C>C(Cl)(Cl)(Cl)Cl>[CH3:12][S:11][C:9]1[C:10]2=[C:2]([CH2:1][N:37]3[CH2:38][CH2:39][CH:34]([OH:33])[CH2:35][CH2:36]3)[CH:3]=[CH:4][N:5]2[N:6]=[CH:7][N:8]=1

Participants

7

Reactant 5

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 79341Piperidin-4-olHCID 81531DiisopropylethylamineHCID 210315125-Methyl-4-(methylsulfanyl)pyrrolo[2,1-f][1,2,4]triazine

Product 1

HCID 21081533HCID 21081533, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of 5-methyl-4-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazine (200 mg, 1.12 mmol), NBS (218 mg, 1.23 mmol), and AIBN (spatula tip) in carbon tetrachloride (4 mL) was heated at 80° C. for 1 h. After cooling to rt, the solution was filtered to remove succinimide. To the filtrate was added 4-hydroxypiperidine (126 mg, 1.34 mmol, Aldrich) and DIPEA (214 μL, 1.23 mmol). The reaction was stirred at rt overnight and was then concentrated in vacuo. The residue was suspended in methanol and filtered. The filtrate was concentrated and the crude product was purified by flash chromatography on silica gel (20% MeOH/EtOAc) to give the title compound (229 mg, 74%) as a colorless solid. 1H NMR (DMSO-d6) δ 8.25 (s, 1H), 7.88 (d, 1H, J=2 Hz), 6.81 (d, 1H, J=2 Hz), 4.54 (br s, 1H), 3.76 (s, 2H), 3.48–3.44 (m, 1H), 2.75–2.71 (m, 2H), 2.62 (s, 3H), 2.10–2.08 (m, 2H), 1.70–1.68 (m, 2H), 1.38–1.36 (m, 2H); MS(ESI+) m/z 279.3 (M+H)+.

Workup

  1. filtrationthe solution was filtered
  2. customto remove succinimide
  3. concentrationwas then concentrated in vacuo
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. customthe crude product was purified by flash chromatography on silica gel (20% MeOH/EtOAc)

Sources & evidence

ORD record
ord-5baf4e2c0ada46eda99830f68dc2c639
Source dataset
uspto-grants-2007_02
Patent number
US07173031B2

Reaction notes

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