Toluene → HCID 23353228, compound

HRID 235070Notes

Reaction equation

HRID 235070 reaction equation
NC1N=[C:6]2[S:8][CH:9]=[CH:10][C:5]2=[N:4]C=1C(OCC)=O.Cl[C:17](Cl)([O:19][C:20](=[O:26])OC(Cl)(Cl)Cl)Cl.C([N:30](CC)CC)C.[C:35]1(C)C=C[CH:38]=[CH:37][CH:36]=1>>[NH2:4][C:5]1[C:10]2[CH:35]=[C:36]([NH2:30])[CH:37]=[CH:38][C:9]=2[S:8][C:6]=1[C:20]([O:19][CH3:17])=[O:26]

Participants

5

Reactant 4

HCID 1140Toluene2×HCID 8471TriethylamineHCID 94429TriphosgeneHCID 23353262HCID 23353262, compound

Product 1

HCID 23353228HCID 23353228, compoundYield 1%

Procedure

Ethyl 3-aminothieno[2,3-b]pyrazine-2-carboxylate (0.43 g, 1.9 mmol) prepared by the method of Schneller and Clough, J. Het. Chem., 12: 513 (1975), triphosgene (0.13 g, 0.43 mmol), triethylamine (0.44 mL, 3.2 mmol), and toluene were stirred at 25° C. for 2 h and then heated to near reflux. Triethylamine hydrochloride was removed by filtration and the filtrate was concentrated. The residue and the product from Example 79A (0.44 g, 1.6 mmol) were taken up in a small amount of toluene. After refuxing for 18 h, the reaction was concentrated and chromatographed (10% EtOH in CH2Cl2) to provide 0.24 g (3 1%) of the title compound which was converted to the HCl salt: m.p. 185° (dec); 1H NMR (300 MHz, CD3OD) δ1.63-1.98 (m, 6H), 2.69-2.85 (m, 3H), 3.20-3.41 (m, 4H), 3.60-3.82 (m, 2H), 3.84 (s, 3H), 4.11-4.16 (m, 3H), 6.77 (d, 1H), 6.81 (d, 1H), 7.16 (t, 1H), 8.77 (d, 1H), 8.84 (d, 1H); MS (DCI/NH3) m/e 478 (M+H)+; Analysis calc'd for C25H27N5O3S.HCl.H2O: C, 56.43; H, 5.68; N, 13.16; found: C, 56.00; H, 5.46; N, 12.78.

Workup

  1. temperatureheated
  2. temperatureto near reflux
  3. customTriethylamine hydrochloride was removed by filtration
  4. concentrationthe filtrate was concentrated
  5. concentrationthe reaction was concentrated
  6. customchromatographed (10% EtOH in CH2Cl2)

Sources & evidence

ORD record
ord-d2be5e26270a4f628e8fdf94a375cbd7
Source dataset
uspto-grants-1997_01
Patent number
US05597823

Reaction notes

Loading…