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Sodium Carbonate → 6-(6-(2,4-Difluorophenyl)imidazo[2,1-b]oxazol-5-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-amine

HRID 1930076
Notes
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Reaction equation

HRID 1930076 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]=[C:11]2[N:15]([C:16]=1[C:17]1[N:18]=[N:19][C:20]([NH:23][NH2:24])=[CH:21][CH:22]=1)[CH:14]=[CH:13][O:12]2.C([O-])([O-])=O.[Na+].[Na+].[N:31]#[C:32]Br>CO>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]=[C:11]2[N:15]([C:16]=1[C:17]1[CH:22]=[CH:21][C:20]3[N:19]([C:32]([NH2:31])=[N:24][N:23]=3)[N:18]=1)[CH:14]=[CH:13][O:12]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 10476Cyanogen BromideHCID 579298696-(2,4-Difluorophenyl)-5-(6-hydrazinylpyridazin-3-yl)imidazo[2,1-b]oxazole

Product 1

HCID 579298906-(6-(2,4-Difluorophenyl)imidazo[2,1-b]oxazol-5-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-amineYield 57%

Reagents, catalysts & solvents 1

HCID 887
Methanol
Solvent

Procedure

The 6-(2,4-difluorophenyl)-5-(6-hydrazinylpyridazin-3-yl)imidazo[2,1-b]oxazole (0.300 g, 0.914 mmol, Example #40, Step B, was dissolved in MeOH (15 mL) at about ambient temperature before addition of Na2CO3 (0.112 g, 1.371 mmol). Cyanogen bromide (3M in DCM, 0.305 mL, 0.914 mmol) was added and the resulting mixture was stirred at about ambient temperature for about 1 h. The crude mixture was partitioned between water and DCM. The organics were dried over MgSO4, filtered, concentrated under reduced pressure to give a yellow solid that was triturated with Et2O and filtered to give the title compound (0.185 g, 57%): LC/MS (Table 1, Method g) Rt=1.65 min.; MS m/z: 354.07 (M+H)+.

Workup

  1. customThe crude mixture was partitioned between water and DCM
  2. dry with materialThe organics were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customto give a yellow solid
  6. customthat was triturated with Et2O
  7. filtrationfiltered

Sources & evidence

ORD record
ord-8fc26fe5cd094bb1ac0bd82246579da1
Source dataset
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08188083B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes