Hydrochloric Acid → HCID 11310529, compound

HRID 1913362Notes

Reaction equation

HRID 1913362 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[S: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[S: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 108994275-(Pyridin-3-yl)thiophene-2-carbaldehyde

Product 1

HCID 11310529HCID 11310529, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 13 (90 mg, 0.48 mmol) was added a solution of dimethylamine (2.9 M, 0.99 mL, 2.85 mmol) in anhydrous CH3OH, a solution of HCl (4.0 M, 0.24 mL, 0.95 mmol) in anhydrous 1,4-dioxane and sodium cyanoborohydride (30 mg, 0.48 mmol). The flask was purged with argon and stirred under an atmosphere of argon at room temperature for 24 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, 2.5/97.5, Rf=0.15) to afford the title compound 42 (57 mg, 55% yield) as a yellow oil: 1H NMR (CDCl3) δ 8.85 (br s, 1H), 8.48 (m, 1H), 7.82 (m, 1H), 7.28 (m, 1H), 7.21 (d, J=3.7 Hz, 1H), 6.91 (d, J=3.5 Hz, 1H), 3.65 (s, 2H) 2.31 (s, 6H); LRMS (ESI) m/z calcd for C12H15N2S [M+H]+ 219. found 219; m/z calcd for C10H8NS [M−N(CH3)2]+ 174. found 174; HRMS (ESI) m/z calcd for C12H15N2S [M+H]+ 219.0956. found 219.0955; HPLC>99% (tR=8.90 min, 55 (A):45 (B): 0.009 (C); tR=6.28 min, 55 (A):45 (B): 0.018 (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, 2.5/97.5, Rf=0.15)

Sources & evidence

ORD record
ord-d07d3fc7610847bda38d6ef7329a9f18
Source dataset
uspto-grants-2013_12
Patent number
US08609708B2

Reaction notes

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