Acetic Acid → HCID 67334083, compound

HRID 1669067Notes

Reaction equation

HRID 1669067 reaction equation
[NH:1]([CH3:3])[CH3:2].[O-:4][N+:5]1[C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][C:9]=2[N:8]=[C:7]([CH2:18][CH2:19][CH:20]=O)[N:6]=1)[CH2:15][CH2:14][CH2:13]3.[BH3-]C#N.[Na+].CC(O)=O>CO>[CH3:2][N:1]([CH3:3])[CH2:20][CH2:19][CH2:18][C:7]1[N:6]=[N+:5]([O-:4])[C:10]2[CH:11]=[C:12]3[C:16]([CH2:15][CH2:14][CH2:13]3)=[CH:17][C:9]=2[N:8]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 674DimethylamineHCID 5003444Sodium cyanoborohydrideHCID 57786560HCID 57786560, compound

Product 1

HCID 67334083HCID 67334083, compoundYield 55.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of anhydrous Me2NH (2.4 g, 52 mmol) in MeOH (50 mL) was added to a solution of propanal 75 (1.5 g, 6.2 mmol) in MeOH (50 ml) at 0° C. and the solution stirred for 20 min. NaCNBH3 (1.5 g, 24 mmol) was added and the solution stirred for 30 min, then HOAc (2 ml) was added and the mixture was stirred at 20° C. for 16 h. The solvent was evaporated and the residue was partitioned between DCM (200 mL) and water (200 mL). The aqueous phase was extracted with DCM (2×200 ml), the combined organic phase was dried and the solvent evaporated. The residue was purified by chromatography, eluting with 10% MeOH/EtOAc, to give 1-oxide 78 (930 mg, 55%) as a yellow oil: 1H NMR [(CD3)2SO] δ 8.17 (s, 1H, H-9), 7.81 (s, 1H, H-5), 3.06-3.12 (m, 4H, H-6, H-8), 2.94-3.03 (m, 4H, 2×CH2), 2.66 [s, 6H, N(CH3)2], 2.07-2.18 (m, 4H, H-7, CH2); 13C NMR δ 164.1, 155.0, 149.2, 146.8, 131.9, 122.4, 113.7, 56.6, 43.0 (2), 33.3, 32.7, 32.4, 25.4, 22.7; HRMS (FAB+) calcd for C15H21N4O (MH+) m/z 273.1715, found 273.1714.

Workup

  1. stirringthe solution stirred for 30 min
  2. stirringthe mixture was stirred at 20° C. for 16 h
  3. customThe solvent was evaporated
  4. customthe residue was partitioned between DCM (200 mL) and water (200 mL)
  5. extractionThe aqueous phase was extracted with DCM (2×200 ml)
  6. customthe combined organic phase was dried
  7. customthe solvent evaporated
  8. customThe residue was purified by chromatography
  9. washeluting with 10% MeOH/EtOAc

Sources & evidence

ORD record
ord-69b566822bab47e3b776f14c3b013a95
Source dataset
uspto-grants-2011_08
Patent number
US07989451B2

Reaction notes

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