Acetic Acid → HCID 69936600, compound

HRID 1623811Notes

Reaction equation

HRID 1623811 reaction equation
[CH3:1][NH:2][CH3:3].C(O)(=O)C.[CH:8]([C:10]1[CH:11]=[CH:12][C:13]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[C:14]([CH:24]=1)[C:15]([NH:17][C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1)=[O:16])=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>ClCCCl.ClCCl>[CH3:1][N:2]([CH2:8][C:10]1[CH:11]=[CH:12][C:13]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[C:14]([CH:24]=1)[C:15]([NH:17][C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1)=[O:16])[CH3:3]

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 674DimethylamineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 86668210HCID 86668210, compound

Product 1

HCID 69936600HCID 69936600, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

Dimethylamine (60 uL, 0.33 mmol) and acetic acid (19 uL, 0.33 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, 0.33 mmol) in DCE (5 ml). The solution was stirred for 3 hours at 50° C. then sodium triacetoxyborohydride (105 mg, 0.50 mmol) was added. The mixture was stirred overnight. Saturated NaHCO3 solution (5 ml) was then added and the mixture was stirred for 5 minutes. The organic layer was diluted with dichloromethane (5 ml), separated and dried (MgSO4). The solvent was removed in vacuo and the residue purified by MDAP to yield the title compound as an opaque solid. 17 mg.

Workup

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

Sources & evidence

ORD record
ord-d1d2f26ccf304bd9950d99fe020b647a
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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