Acetic Acid → HCID 69936766, compound

HRID 1623809Notes

Reaction equation

HRID 1623809 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C(O)(=O)C.[CH:11]([C:13]1[CH:14]=[CH:15][C:16]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[C:17]([CH:27]=1)[C:18]([NH:20][C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1)=[O:19])=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>ClCCCl.ClCCl>[N:1]1([CH2:11][C:13]2[CH:14]=[CH:15][C:16]([O:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[C:17]([CH:27]=2)[C:18]([NH:20][C:21]2[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=2)=[O:19])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 8083MorpholineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 86668210HCID 86668210, compound

Product 1

HCID 69936766HCID 69936766, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

Morpholine (26 uL, 0.30 mmol) and acetic acid (17 ul, 0.30 mmol) were added to a solution of 5-formyl-2-[(phenylmethyl)oxy]-N-3-pyridinylbenzamide (may be prepared as described in Example 66; 100 mg, 0.301 mmol) in DCE (5 ml). The solution was stirred for 4 hours at 50° C. then sodium triacetoxyborohydride (96 mg, 0.45 mmol) was added. The reaction was stirred overnight. Saturated NaHCO3 solution (5 ml) was added and the mixture stirred for 5 minutes. The organic layer was then diluted with dichloromethane (5 ml) before being separated and dried (MgSO4). The solvent was removed in vacuo and the residue purified by MDAP to yield the title compound. 40 mg.

Workup

  1. stirringThe reaction was stirred overnight
  2. stirringthe mixture stirred for 5 minutes
  3. custombefore being separated
  4. dry with materialdried (MgSO4)
  5. customThe solvent was removed in vacuo
  6. customthe residue purified by MDAP

Sources & evidence

ORD record
ord-5824787b23fa41029d67c06b88bdcd0a
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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