Acetic Acid → HCID 58873186, compound

HRID 1990103Notes

Reaction equation

HRID 1990103 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[S:7][C:8]([CH2:25][CH3:26])=[C:9](C#N)[C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([C:17]2[S:18][CH:19]=[CH:20][C:21]=2N)=[CH:13][CH:12]=1)=[O:5])[CH3:2].[CH2:27]=O.[C:29]([BH3-])#[N:30].[Na+].C(O)(=O)C.[C:37](#[N:39])C>O>[CH2:1]([O:3][C:4]([C:6]1[S:7][C:8]([CH2:25][CH3:26])=[C:9]([C:29]#[N:30])[C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([C:17]2[S:18][CH:19]=[CH:20][C:21]=2[N:39]([CH3:37])[CH3:27])=[CH:13][CH:12]=1)=[O:5])[CH3:2]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 712FormaldehydeHCID 6342AcetonitrileHCID 5003444Sodium cyanoborohydrideHCID 68525014HCID 68525014, compound

Product 1

HCID 58873186HCID 58873186, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Prepare with procedure described in literature Sznaidman M. L.; Meade E. A.; Beauchamp, L. M.; Russell, R.; Tisdale, M., Bioorg. Med. Chem. Lett., 1996, 6, 5, 565-568. Stir at room temperature under nitrogen a mixture of 3-[4-(3-amino-thiophen-2-yl)-phenyl]-4-cyano-5-ethyl-thiophene-2-carboxylic acid ethyl ester (0.05 g, 0.131 mmol), paraformaldehyde (0.041 g, 1.31 mmol), sodium cyanoborohydride (0.026 g, 0.393 mmol) and acetic acid (0.02 mL, 0.262 mmol) in dry acetonitrile (1 mL). After 3 h add water and extract with ethyl acetate. Combine the organic layers, dry over sodium sulfate, filter and concentrate under reduced pressure to give a residue. Purify the residue by flash chromatography (silica gel) eluting with ethyl acetate:hexane 1:2 to provide the title compound (0.033 g, 61%). Mass spectrum (m/e): 411 (M+1). 1H-NMR (CDCl3) δ1.19 (t, 3H, J=7.2 Hz); 1.44 (t, 3H, J=7.5 Hz); 2.71 (s, 6H); 3.09 (c, 2H, J=7.5 Hz); 4.20 (c, 2H, J=7.2 Hz); 6.97 (d, 1H, J=5.4 Hz); 7.19 (d, 1H, J=5.6 Hz); 7.38-7.43 (m, 2H); 7.81-7.86 (m, 2H).

Workup

  1. customPrepare with procedure
  2. extractionextract with ethyl acetate
  3. dry with materialdry over sodium sulfate
  4. filtrationfilter
  5. concentrationconcentrate under reduced pressure
  6. customto give a residue
  7. customPurify the residue by flash chromatography (silica gel)
  8. washeluting with ethyl acetate:hexane 1:2

Sources & evidence

ORD record
ord-8881236ad2614a45967bc16d798b980e
Source dataset
uspto-grants-2010_01
Patent number
US07642361B2

Reaction notes

Loading…