Acetic Acid → HCID 69936603, compound

HRID 1623855Notes

Reaction equation

HRID 1623855 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:26]=[N:27][CH:28]=[CH:29][CH:30]=2)=[O:23])=[CH:14][CH:13]=1.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:17]=[CH:16][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:26]=[N:27][CH:28]=[CH:29][CH:30]=2)=[O:23])=[CH:14][CH:13]=1

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 8083MorpholineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 86668208HCID 86668208, compound

Product 1

HCID 69936603HCID 69936603, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

Morpholine (0.05 ml, 0.57 mmol) and acetic acid (0.03 ml, 0.57 mmol) were added to a solution of 2-{[(4-fluorophenyl)methyl]oxy}-5-formyl-N-3-pyridinylbenzamide (may be prepared Example 82; 200 mg, 0.57 mmol) in DCE (5 ml) and the mixture was stirred at room temperature for 10 min. Sodium triacetoxyborohydride (181 mg, 0.86 mmol) was then added and the mixture was warmed to 50° C. overnight. Saturated sodium hydrogencarbonate (10 ml) was added and the mixture was 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 organics were combined and evaporated under reduced pressure. The residue was purified by MDAP to yield the title compound. 150 mg.

Workup

  1. temperaturethe mixture was warmed to 50° C. overnight
  2. stirringthe mixture was 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-87480e4f6bc64cb2b0f091cb7fa71d19
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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