Triphenylphosphine → 4-((6-(3-Fluoro-4-(2-morpholinoethoxy)phenyl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methoxy)-7-methoxyquinoline

HRID 2176486Notes

Reaction equation

HRID 2176486 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][O:7][CH2:6][CH2:5]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[F:29][C:30]1[CH:35]=[C:34]([C:36]2[CH:37]=[CH:38][C:39]3[N:40]([C:42]([CH2:45][O:46][C:47]4[C:56]5[C:51](=[CH:52][C:53]([O:57][CH3:58])=[CH:54][CH:55]=5)[N:50]=[CH:49][CH:48]=4)=[N:43][N:44]=3)[N:41]=2)[CH:33]=[CH:32][C:31]=1O.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[F:29][C:30]1[CH:35]=[C:34]([C:36]2[CH:37]=[CH:38][C:39]3[N:40]([C:42]([CH2:45][O:46][C:47]4[C:56]5[C:51](=[CH:52][C:53]([O:57][CH3:58])=[CH:54][CH:55]=5)[N:50]=[CH:49][CH:48]=4)=[N:43][N:44]=3)[N:41]=2)[CH:33]=[CH:32][C:31]=1[O:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][O:7][CH2:6][CH2:5]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 611632-MorpholinoethanolHCID 5462977Diethyl azodicarboxylateHCID 135955104HCID 135955104, compound

Product 1

HCID 250651344-((6-(3-Fluoro-4-(2-morpholinoethoxy)phenyl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methoxy)-7-methoxyquinoline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 4-(2-hydroxyethyl)morpholine (0.0964 ml, 0.788 mmol), triphenylphosphine (0.238 g, 0.909 mmol), 2-fluoro-4-(3-((7-methoxyquinolin-4-yloxy)methyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)phenol (0.253 g, 0.606 mmol)(prepared according to General Method A) in THF (10 mL) was added DEAD (0.144 ml, 0.909 mmol). Stirred at room temperature for 1 h. Concentrated. Purified on RPHPLC. Fractions containing product were treated with 9% sodium carbonate. Removed volatiles in vacuo. Product crashed out and was isolated by filtration. MS m/z=531.2 [M+1]+. Calc'd for C28H27FN6O4: 530.5.

Workup

  1. concentrationConcentrated
  2. customPurified on RPHPLC
  3. additionFractions containing product
  4. additionwere treated with 9% sodium carbonate
  5. customwas isolated by filtration

Sources & evidence

ORD record
ord-e92cb87e99914421828c92bc7e1301d7
Source dataset
uspto-grants-2015_06
Patent number
US09066954B2

Reaction notes

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