HCID 57691296, compound → HCID 57691164, compound

HRID 1513751Notes

Reaction equation

HRID 1513751 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[N:5][C:6]2[C:11]([CH:12]=1)=[CH:10][C:9]([C:13]([CH3:31])([CH3:30])[C:14]([NH:16][NH:17][C:18]1[N:19]=[N:20][C:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:22][CH:23]=1)=O)=[CH:8][CH:7]=2>C(O)(C(F)(F)F)=O>[CH3:1][O:2][C:3]1[CH:4]=[N:5][C:6]2[C:11]([CH:12]=1)=[CH:10][C:9]([C:13]([C:14]1[N:19]3[N:20]=[C:21]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[CH:22]=[CH:23][C:18]3=[N:17][N:16]=1)([CH3:31])[CH3:30])=[CH:8][CH:7]=2

Participants

3

Reactant 1

HCID 57691296HCID 57691296, compound

Product 1

HCID 57691164HCID 57691164, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 2-(3-methoxyquinolin-6-yl)-2-methyl-N′-(6-phenylpyridazin-3-yl)propanehydrazide (270 mg, 653 μmol) in TFA (2 mL) was heated to 150° C. in microwave (6 bar; 20 W) for 2 h. LCMS suggests very good conversion: 89425-17-1. Reaction concentrated under reduced pressure then partitioned between CHCl3/IPA (50 mL) and 1M NaOH (50 mL). Aqueous further extracted with CHCl3/IPA (15 mL) and combined organics dried over MgSO4, concentrated, then dissolved in ACN (2 mL). Crystallized solid washed with ACN (1 mL) and dried under reduced pressure. MS (ESI pos. ion) m/z: 396 (MH+). Calc'd exact mass for C24H21N5O: 395.

Workup

  1. customReaction
  2. concentrationconcentrated under reduced pressure
  3. customthen partitioned between CHCl3/IPA (50 mL) and 1M NaOH (50 mL)
  4. extractionAqueous further extracted with CHCl3/IPA (15 mL)
  5. dry with materialcombined organics dried over MgSO4
  6. concentrationconcentrated
  7. dissolutiondissolved in ACN (2 mL)
  8. customCrystallized solid
  9. washwashed with ACN (1 mL)
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-5f669f6d44f74285859e0a38f53d8161
Source dataset
uspto-grants-2012_07
Patent number
US08217177B2

Reaction notes

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