Dimethylformamide → Tert-butyl (6-carbamoyl-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methylcarbamate

HRID 2176699Notes

Reaction equation

HRID 2176699 reaction equation
[C:1]([O:5][C:6](CC1N2N=C(C(O)=O)C=CC2=N[N:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C([O:28][N:29]1[N:37]=[N:36][C:31]2[CH:32]=[CH:33][CH:34]=[N:35][C:30]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C([N:47]([CH2:50]C)CC)C.C[N:53]([CH:55]=[O:56])C>>[CH3:1][OH:5].[NH4+:10].[OH-:28].[C:55]([C:31]1[CH:32]=[CH:33][C:34]2[N:35]([C:30]([CH2:50][NH:47][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[N:29][N:37]=2)[N:36]=1)(=[O:56])[NH2:53]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 675033743-((Tert-butoxycarbonyl)methyl)-[1,2,4]triazolo[4,3-b]pyridazine-6-carboxylic acid

Product 2

HCID 21894508Ammonium hydroxide methanolYield 1%HCID 57691087Tert-butyl (6-carbamoyl-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methylcarbamateYield 52%

Procedure

In a 10 mL round bottom flask under N2 were dissolved 3-((tert-butoxycarbonyl)methyl)-[1,2,4]triazolo[4,3-b]pyridazine-6-carboxylic acid (250 mg, 852 μmol), HATU (389 mg, 1023 μmol), triethylamine (356 μl, 2557 μmol) in 1.5 mL of DMF then was treated with a (92 μl, 4262 μmol) and stirred at t. After 2 h the reaction mixture based on LC-MS was concentrated under reduced pressure and then purified by MPLC (ISCO) with DCM:MeOH+NH4OH (1%) 100:0 to 90:10 to afforded tert-butyl (6-carbamoyl-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methylcarbamate (129 mg, 52% yield). MS m/z=293.2 [M+1]+. Calc'd for C12H16N6O3: 292.3.

Workup

  1. additionthen was treated with a (92 μl, 4262 μmol)
  2. concentrationwas concentrated under reduced pressure
  3. custompurified by MPLC (ISCO) with DCM

Sources & evidence

ORD record
ord-7a761f4583a6479590a397a093caf870
Source dataset
uspto-grants-2015_06
Patent number
US09066954B2

Reaction notes

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