Toluene → HCID 57691362, compound

HRID 219115Notes

Reaction equation

HRID 219115 reaction equation
[C:1]1([C:7]2[CH:8]=[N:9][C:10]3[N:11]([C:13]([CH2:16]O)=[N:14][N:15]=3)[N:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.C(N1C=C(C2C=CC3N(C(CN)=[N:34][N:35]=3)N=2)C=N1)(C)C.C1CCN2C(=[N:42]CCC2)CC1.C1(C)C=CC=CC=1>>[N:42]([CH2:16][C:13]1[N:11]2[N:12]=[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH:8]=[N:9][C:10]2=[N:15][N:14]=1)=[N+:34]=[N-:35]

Participants

5

Reactant 4

HCID 1140TolueneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 675025246-Phenyl-1,2,4-triazolo[4,3-b][1,2,4]triazine-3-methanolHCID 67503644(6-(1-isopropyl-1H-pyrazol-4-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methanamine hydrochloride

Product 1

HCID 57691362HCID 57691362, compound

Procedure

A 16 mm test tube was charged with (6-phenyl-[1,2,4]triazolo[4,3-b][1,2,4]triazin-3-yl)methanol (0.500 g, 2.20 mmol), Reactant 2 (0.951 ml, 4.40 mmol), DBU (0.663 ml, 4.40 mmol), and toluene (8.16 ml, 77.0 mmol), flushed with argon, sealed, then stirred at room temperature for 3 hours. The dark maroon mixture was concentrated and the resulting dark purple/black oil was purified by column chromatography using a gradient of 3-5% MeOH/DCM over 20 minutes. 3-(azidomethyl)-6-phenyl-[1,2,4]triazolo[4,3-b][1,2,4]triazine was isolated as a brown solid.

Workup

  1. customflushed with argon
  2. customsealed
  3. concentrationThe dark maroon mixture was concentrated
  4. customthe resulting dark purple/black oil was purified by column chromatography
  5. customover 20 minutes

Sources & evidence

ORD record
ord-87b2684516bf45e3b9d0dd17b61f8607
Source dataset
uspto-grants-2012_06
Patent number
US08198448B2

Reaction notes

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