Hydrochloric Acid → HCID 11171679, compound

HRID 1913363Notes

Reaction equation

HRID 1913363 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[O:11][C:10]([CH:12]=O)=[CH:9][CH:8]=2)[CH:2]=1.[CH3:14][NH:15][CH3:16].Cl.C([BH3-])#N.[Na+]>CO.O1CCOCC1>[CH3:14][N:15]([CH3:16])[CH2:12][C:10]1[O:11][C:7]([C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 674DimethylamineHCID 5003444Sodium cyanoborohydrideHCID 122152605-(Pyridin-3-yl)furan-2-carbaldehyde

Product 1

HCID 11171679HCID 11171679, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 23 (54 mg, 0.31 mmol) was added a solution of dimethylamine (2.9 M, 0.65 mL, 1.89 mmol) in anhydrous CH3OH, a solution of HCl (4.0 M, 0.16 mL, 0.63 mmol) in anhydrous 1,4-dioxane and sodium cyanoborohydride (20 mg, 0.31 mmol). The flask was purged with argon and stirred under an atmosphere of argon at room temperature for 48 h. The solution was adjusted to pH 2 with conc. HCl and the solvent was removed in vacuo. The residue was dissolved in water, washed with Et2O (3×10 mL), adjusted to pH 10 with NaOH(aq) (10 N), extracted with Et2O (3×20 mL), dried (Na2SO4), filtered and the solvent was removed in vacuo. The crude material was chromatographed on silica gel (CH3OH/CHCl3, 5/95, Rf=0.2) to afford the title compound 43 (23 mg, 37% yield) as a yellow oil: 1H NMR (CDCl3) δ 8.91 (m, 1H), 8.46 (m, 1H), 7.94 (m, 1H), 7.28 (m, 1H), 6.68 (d, J=3.3 Hz, 1H), 6.32 (d, J=3.4 Hz, 1H), 2.31 (s, 6H); LRMS (ESI) m/z calcd for C12H15N2O [M+H]+ 203. found 203; m/z calcd for C10H8NO [M−N(CH3)2]+ 158. found 158; HRMS (ESI) m/z calcd for C12H15N2O [M+H]+ 203.1184. found 203.1205; HPLC>99% (tR=6.00 min, 60 (A):40 (B): 0.07 (C); tR=5.10 min, 60 (A):40 (B): 0.1 (C)).

Workup

  1. customThe flask was purged with argon
  2. customthe solvent was removed in vacuo
  3. dissolutionThe residue was dissolved in water
  4. washwashed with Et2O (3×10 mL)
  5. extractionextracted with Et2O (3×20 mL)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customthe solvent was removed in vacuo
  9. customThe crude material was chromatographed on silica gel (CH3OH/CHCl3, 5/95, Rf=0.2)

Sources & evidence

ORD record
ord-b1b4f98b99134ac3a6c07328211c7b56
Source dataset
uspto-grants-2013_12
Patent number
US08609708B2

Reaction notes

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