Morpholine → HCID 57929959, compound

HRID 1930002Notes

Reaction equation

HRID 1930002 reaction equation
CS(O[CH2:6][CH2:7][N:8]1[CH:12]=[C:11]([C:13]2[CH:14]=[CH:15][C:16]3[N:17]([C:19]([CH:22]([CH3:24])[CH3:23])=[N:20][N:21]=3)[N:18]=2)[C:10]([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:26]=2[F:32])=[N:9]1)(=O)=O.[NH:33]1[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1>CO>[F:32][C:26]1[CH:27]=[C:28]([F:31])[CH:29]=[CH:30][C:25]=1[C:10]1[C:11]([C:13]2[CH:14]=[CH:15][C:16]3[N:17]([C:19]([CH:22]([CH3:23])[CH3:24])=[N:20][N:21]=3)[N:18]=2)=[CH:12][N:8]([CH2:7][CH2:6][N:33]2[CH2:38][CH2:37][O:36][CH2:35][CH2:34]2)[N:9]=1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 57929849HCID 57929849, compound

Product 1

HCID 57929959HCID 57929959, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

The 2-(3-(2,4-difluorophenyl)-4-(3-isopropyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)-1H-pyrazol-1-yl)ethyl methanesulfonate (0.24 g, 0.52 mmol; Preparation #W.1) was dissolved in MeOH (4 mL) then morpholine (0.36 g, 4.2 mmol) was added. The mixture was heated at about 70° C. in an oil bath for about 2 h then cooled and concentrated under reduced pressure. The crude material was purified by RP-HPLC (Table 1, Method d). The appropriate fractions were concentrated under reduced pressure then basified with 2 N NaOH. Extraction of the solution with EtOAc followed by drying of the organic extract over MgSO4 and then filtration prior to concentrating under reduced pressure gave the title compound (0.10 g, 43%): LC/MS (Table 1, Method a) Rt=2.09 min; MS m/z: 454.2 (M+H)+.

Workup

  1. temperaturethen cooled
  2. concentrationconcentrated under reduced pressure
  3. customThe crude material was purified by RP-HPLC (Table 1, Method d)
  4. concentrationThe appropriate fractions were concentrated under reduced pressure
  5. extractionExtraction of the solution with EtOAc
  6. customby drying of the
  7. extractionorganic extract over MgSO4
  8. filtrationfiltration
  9. concentrationto concentrating under reduced pressure

Sources & evidence

ORD record
ord-848b6908dfc442ec91c2b53f4239de51
Source dataset
uspto-grants-2012_05
Patent number
US08188083B2

Reaction notes

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