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Nitroethane → Tert-butyl (6-(3-methylisoxazol-5-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methylcarbamate

HRID 40205
Notes
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Reaction equation

HRID 40205 reaction equation
[N+:1]([CH2:4][CH3:5])([O-:3])=O.C1(N=C=O)C=CC=CC=1.[C:15]([C:17]1[CH:18]=[CH:19][C:20]2[N:21]([C:23]([CH2:26][NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[N:24][N:25]=2)[N:22]=1)#[CH:16].C(N(CC)CC)C>C1C=CC=CC=1>[C:30]([O:29][C:28](=[O:34])[NH:27][CH2:26][C:23]1[N:21]2[N:22]=[C:17]([C:15]3[O:3][N:1]=[C:4]([CH3:5])[CH:16]=3)[CH:18]=[CH:19][C:20]2=[N:25][N:24]=1)([CH3:33])([CH3:32])[CH3:31]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6587NitroethaneHCID 7672Phenyl isocyanateHCID 8471TriethylamineHCID 57691050tert-Butyl (6-ethynyl-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methylcarbamate

Product 1

HCID 57691036Tert-butyl (6-(3-methylisoxazol-5-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methylcarbamate

Reagents, catalysts & solvents 1

HCID 241
Benzene
Solvent

Conditions

Temperature
50 °C

Procedure

To a solution of nitroethane (1.02 ml, 14.3 mmol) in benzene (50 mL) was added phenyl isocyanate (3.12 ml, 28.5 mmol). The mixture was stirred at 50° C. for twenty minutes followed by the addition of tert-butyl (6-ethynyl-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methylcarbamate (3.00 g, 11.0 mmol) and triethylamine (0.0765 ml, 0.549 mmol). The mixture was stirred at 50° C. for six hours then at room temperature overnight. The mixture was cooled to room temperature, filtered and the resulting brown precipitate was washed with additional benzene. The filtrate was concentrated to yield the product as a black solid. MS m/z=331.1 [M+1]+. Calc'd for C15H18N6O3: 330.1.

Workup

  1. stirringThe mixture was stirred at 50° C. for six hours
  2. customat room temperature
  3. customovernight
  4. temperatureThe mixture was cooled to room temperature
  5. filtrationfiltered
  6. washthe resulting brown precipitate was washed with additional benzene
  7. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-d952825d729b4d20be4a45b727aa6332
Source dataset
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08524900B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes