Acetic Acid → HCID 68585790, compound

HRID 17325Notes

Reaction equation

HRID 17325 reaction equation
C=O.[C:3]([C:7]1[O:8][C:9]2[C:10](=[C:12]([C:29]#[N:30])[C:13]([CH3:28])=[C:14]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:15]=2[N:16]2[CH2:19][CH:18]([NH:20][CH3:21])[CH2:17]2)[N:11]=1)([CH3:6])([CH3:5])[CH3:4].[C:31]([BH3-])#N.[Na+].C(O)(=O)C.C(=O)([O-])[O-].[Na+].[Na+]>[Cl-].[Na+].O.CO>[C:3]([C:7]1[O:8][C:9]2[C:10](=[C:12]([C:29]#[N:30])[C:13]([CH3:28])=[C:14]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:15]=2[N:16]2[CH2:17][CH:18]([N:20]([CH3:31])[CH3:21])[CH2:19]2)[N:11]=1)([CH3:6])([CH3:4])[CH3:5]

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 712FormaldehydeHCID 10340Sodium CarbonateHCID 5003444Sodium cyanoborohydrideHCID 685840002-tert-Butyl-5-methyl-7-(3-methylaminoazetidin-1-yl)-6-phenyl-1,3-benzoxazole-4-carbonitrile

Product 1

HCID 68585790HCID 68585790, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
0 °C

Procedure

Aqueous 36% formaldehyde solution (205 μl, 2.75 mmol) was added to a methanol (4 ml) solution of 2-tert-butyl-5-methyl-7-(3-methylaminoazetidin-1-yl)-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-73) (103 mg, 275 μmol), followed by cooling at 0° C. Sodium cyanoborohydride (34.6 mg, 550 μmol) and acetic acid (40.9 μl, 715 μmol) were added, followed by stirring at room temperature for 20 minutes. Aqueous 10% sodium carbonate solution and saturated brine were added to the reaction liquid, and this was extracted with ethyl acetate and chloroform. The organic layers were combined, dried over anhydrous magnesium sulfate, concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (chloroform:methanol=200:1), again purified by silica gel column chromatography (dichloromethane:ethyl acetate=1:1) to obtain the entitled compound (94 mg, 88%) as a colorless solid.

Workup

  1. extractionthis was extracted with ethyl acetate and chloroform
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (chloroform:methanol=200:1)
  5. customagain purified by silica gel column chromatography (dichloromethane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-aa314d9d38e24de0969d47d7dc94b2a9
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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