HCID 59004663, compound → HCID 178480247, compound

HRID 1668459Notes

Reaction equation

HRID 1668459 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[CH2:8][CH2:9][N:10]1[C:18]2[C:13](=[CH:14][C:15]([NH2:19])=[CH:16][CH:17]=2)[CH:12]=[CH:11]1.I.[S:21]1[CH:25]=[CH:24][CH:23]=[C:22]1[C:26](SC)=[NH:27]>CCO>[CH3:1][N:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[CH2:8][CH2:9][N:10]1[C:18]2[C:13](=[CH:14][C:15]([NH:19][C:26]([C:22]3[S:21][CH:25]=[CH:24][CH:23]=3)=[NH:27])=[CH:16][CH:17]=2)[CH:12]=[CH:11]1

Participants

4

Reactant 2

HCID 59004663HCID 59004663, compoundHCID 66704664Methyl thiophene-2-carbimidothioate hydroiodide

Product 1

HCID 178480247HCID 178480247, compoundYield 46.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of compound 61 (235 mg, 0.91 mmol) in EtOH (10 mL) was treated with methyl thiophene-2-carbimidothioate hydroiodide (520 mg, 1.83 mmol) and stirred overnight at room temperature. Argon was bubbled through the mixture for 20 minutes then it was concentrated to give brownish oil. This residue was partitioned between CH2Cl2 (50 mL) with 10% MeOH and saturated sodium bicarbonate (20 mL). The aqueous layer was extracted with an additional CH2Cl2 (50 mL). The combined organic layers were washed with brine, dried over sodium sulfate and concentrated to give a brown residue which was subjected to flash chromatography on silica gel (MeOH:CH2Cl2, 5:95 to 2M NH3 in MeOH:CH2Cl2, 1:9) to give compound 62 (154 mg, 46.1%) as a yellow solid. 1H NMR (DMSO-d6) δ 7.71 (d, J=2.9 Hz, 1H), 7.58 (d, J=5.1 Hz, 1H), 7.37-7.30 (m, 2H), 7.10-7.08 (m, 1H), 6.98 (s, 1H), 6.70 (dd, J=1.5, 6.9 Hz, 1H), 6.31 (d, J=3.0 Hz, 1H), 6.25 (brs, 2H), 4.15 (t, J=7.5 Hz, 2H), 2.79-2.75 (m, 1H), 2.19 (s, 3H), 2.05-1.15 (m, 10H); ESI-MS (m/z, %): 367 (M+1,50), 184 (M+2, 100); ESI-HRMS calculated for C21H27N4S (MH+): 367.1966, observed: 367.1937.

Workup

  1. customArgon was bubbled through the mixture for 20 minutes
  2. concentrationit was concentrated
  3. customto give brownish oil
  4. customThis residue was partitioned between CH2Cl2 (50 mL) with 10% MeOH and saturated sodium bicarbonate (20 mL)
  5. extractionThe aqueous layer was extracted with an additional CH2Cl2 (50 mL)
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated
  9. customto give a brown residue which

Sources & evidence

ORD record
ord-321377ca5a974e1b9989b663fef1f47b
Source dataset
uspto-grants-2011_08
Patent number
US07989447B2

Reaction notes

Loading…