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

HRID 219272
Notes
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Reaction equation

HRID 219272 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]2[N:8]([C:10]([CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[N:11][N:12]=2)[N:9]=1)(=[O:3])[NH2:2].C([O:26]C(CC1N2N=C(C(O)=O)C=CC2=NN=1)=O)(C)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>CN(C=O)C>[CH3:1][OH:3].[NH4+:2].[OH-:26].[C:1]([C:4]1[CH:5]=[CH:6][C:7]2[N:8]([C:10]([CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:19])([CH3:18])[CH3:20])=[N:11][N:12]=2)[N:9]=1)(=[O:3])[NH2:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57691087Tert-butyl (6-carbamoyl-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methylcarbamateHCID 675033743-((Tert-butoxycarbonyl)methyl)-[1,2,4]triazolo[4,3-b]pyridazine-6-carboxylic acid

Product 2

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-((tert-butoxycarbonyl)methyl)-[1,2,4]triazolo[4,3-b]pyridazine-6-carboxylic acid. In a 25 mL round bottom flask were dissolved 2-methyl-2-butene (21639 μl, 43278 μmol), potassium dihydrogen phosphate (2356 mg, 17311 μmol) and tert-butyl (6-formyl-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methylcarbamate (600 mg, 2164 μmol) in 5 mL of t-BuOH and 5 mL of water then was added at 0° C. sodium chlorite (783 mg, 8656 μmol) and the reaction mixture was warmed to rt. After 10 h the reaction mixture based on LC-MS was concentrated under reduced pressure and the crude acid was extract from the solid salts mixture with MeOH, filtered and the solvent was concentrated under reduced pressure. The crude 3-((tert-butoxycarbonyl)methyl)-[1,2,4]triazolo[4,3-b]pyridazine-6-carboxylic acid (635 mg, 100% yield) was used without further purification in the next step. MS m/z=294.2 [M+1]+. Calc'd for C12H15N5O4: 293.1 b) tert-butyl (6-carbamoyl-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methylcarbamate. 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 rt. 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-7d2a6e7fdf3e46f19af64e83448d700f
Source dataset
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08198448B2

Reaction notes

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