Acetic Acid → HCID 69936478, compound

HRID 1623850Notes

Reaction equation

HRID 1623850 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:13]=[C:14]([CH2:19][O:20][C:21]2[CH:35]=[CH:34][C:33]([CH:36]=O)=[CH:32][C:22]=2[C:23]([NH:25][C:26]2[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=2)=[O:24])[CH:15]=[CH:16][C:17]=1[F:18].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>ClCCCl.ClCCl>[F:11][C:12]1[CH:13]=[C:14]([CH2:19][O:20][C:21]2[CH:35]=[CH:34][C:33]([CH2:36][N:1]3[CH2:6][CH2:5][O:4][CH2:3][CH2:2]3)=[CH:32][C:22]=2[C:23]([NH:25][C:26]2[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=2)=[O:24])[CH:15]=[CH:16][C:17]=1[F:18]

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 8083MorpholineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 86668212HCID 86668212, compound

Product 1

HCID 69936478HCID 69936478, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

Morpholine (0.05 ml, 0.54 mmol) and acetic acid (0.03 ml, 0.54 mmol) were added to solution of 2-([(3,4-difluorophenyl)methyl]oxy)-5-formyl-N-3-pyridinylbenzamide (may be prepared by Example 80; 200 mg, 0.54 mmol) in DCE (5 ml), and the mixture was stirred at room temperature for 10 min. Sodium triacetoxyborohydride (173 mg, 0.81 mmol) was then added and the mixture was warmed to 50° C. overnight. Saturated sodium hydrogencarbonate (10 ml) was added and the mixture stirred for 10 min before being diluted with dichloromethane (25 ml). The organic layer was separated and the aqueous phase was extracted with dichloromethane (25 ml), the organic were combined and evaporated under reduced pressure. The residue was purified by MDAP to yield the title compound. 82 mg.

Workup

  1. temperaturethe mixture was warmed to 50° C. overnight
  2. stirringthe mixture stirred for 10 min
  3. customThe organic layer was separated
  4. extractionthe aqueous phase was extracted with dichloromethane (25 ml)
  5. customevaporated under reduced pressure
  6. customThe residue was purified by MDAP

Sources & evidence

ORD record
ord-f1efab976922497c8f4d77e5b2ca5f5f
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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