Acetic Acid → HCID 44252988, compound

HRID 76947Notes

Reaction equation

HRID 76947 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([N:23]([CH3:25])[CH3:24])[CH2:14][CH2:13][C:12]([NH:21][CH3:22])([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.C=O.[C:28](B)#N.[Na].C(O)(=O)C>C(#N)C>[CH3:22][N:21]([CH3:28])[C:12]1([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:11][CH2:10][C:9]([N:23]([CH3:25])[CH3:24])([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)[CH2:14][CH2:13]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 44252839HCID 44252839, compoundHCID 101953985CID 101953985

Product 1

HCID 44252988HCID 44252988, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of the title compound from Example 68 (96 mg, 0.28 mmol) and formalin (0.39 mL, 37% aqueous solution) in acetonitrile (3 mL) was mixed with sodium cyanoboron hydride (72 mg, 1.15 mmol) and stirred for 45 min at RT. Conc. acetic acid was then added until a neutral reaction occurred and the mixture stirred for 45 min at RT. For work up the solvent was removed in a vacuum, the residue taken up in 2N NaCl (5 mL) and then extracted with ether (3×10 mL). The organic solution was dried over Na2SO4 and concentrated to low volume in a vacuum. The remaining residue was purified by means of flash chromatography with ethyl acetate/methanol (2:1→1:1→1:1+2% NH3).

Workup

  1. stirringthe mixture stirred for 45 min at RT
  2. customFor work up the solvent was removed in a vacuum
  3. extractionextracted with ether (3×10 mL)
  4. dry with materialThe organic solution was dried over Na2SO4
  5. concentrationconcentrated to low volume in a vacuum
  6. customThe remaining residue was purified by means of flash chromatography with ethyl acetate/methanol (2:1→1:1→1:1+2% NH3)

Sources & evidence

ORD record
ord-cb0f3a6437f14342aa4c3169e0e4f463
Source dataset
uspto-grants-2014_09
Patent number
US08835689B2

Reaction notes

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