Acetic Acid → HCID 69936546, compound

HRID 1623857Notes

Reaction equation

HRID 1623857 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C(O)(=O)C.[F:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][O:19][C:20]2[CH:34]=[CH:33][C:32]([CH:35]=O)=[CH:31][C:21]=2[C:22]([NH:24][C:25]2[CH:30]=[CH:29][N:28]=[N:27][CH:26]=2)=[O:23])=[CH:14][CH:13]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.ClCCl.C(=O)([O-])O.[Na+]>[F:11][C:12]1[CH:13]=[CH:14][C:15]([CH2:18][O:19][C:20]2[CH:34]=[CH:33][C:32]([CH2:35][N:1]3[CH2:6][CH2:5][O:4][CH2:3][CH2:2]3)=[CH:31][C:21]=2[C:22]([NH:24][C:25]2[CH:30]=[CH:29][N:28]=[N:27][CH:26]=2)=[O:23])=[CH:16][CH:17]=1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 8083MorpholineHCID 5049666Sodium triacetoxyborohydrideHCID 86668214HCID 86668214, compound

Product 1

HCID 69936546HCID 69936546, compound

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Morpholine (0.07 ml, 0.85 mmol) followed by acetic acid (0.03 ml, 0.57 mmol) were added to a suspension of 2-([(4-fluorophenyl)methyl]oxy)-5-formyl-N-4-pyridazinylbenzamide (may be prepared as described in Example 84; 200 mg, 0.57 mmol) in DCE (10 ml). The mixture was stirred at room temperature for 10 min and then sodium triacetoxyborohydride (133 mg, 0.63 mmol) was added. The mixture was warmed to 50° C. for 3 hrs. The reaction mixture was diluted with dichloromethane (25 ml) and saturated sodium hydrogen carbonate was added to this mixture until no effevervesence was observed. The mixture was separated and the organic layer was evaporated under reduced pressure. The residue was purified using MDAP to yield the title compound. 180 mg.

Workup

  1. temperatureThe mixture was warmed to 50° C. for 3 hrs
  2. additionwas added to this mixture until no effevervesence
  3. customThe mixture was separated
  4. customthe organic layer was evaporated under reduced pressure
  5. customThe residue was purified

Sources & evidence

ORD record
ord-2a0b12d824ac44fe9447a43093862176
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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