Tetrahydrofuran → HCID 66937230, compound

HRID 408680Notes

Reaction equation

HRID 408680 reaction equation
[Cl:1][C:2]1[NH:6][C:5]2[CH:7]=[CH:8][CH:9]=[C:10]([Cl:11])[C:4]=2[N:3]=1.C1COCC1.CCN(C(C)C)C(C)C.Cl[CH2:27][O:28][CH2:29][CH2:30][O:31][CH3:32]>CCOC(C)=O>[Cl:1][C:2]1[N:6]([CH2:27][O:28][CH2:29][CH2:30][O:31][CH3:32])[C:5]2[CH:7]=[CH:8][CH:9]=[C:10]([Cl:11])[C:4]=2[N:3]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 81531DiisopropylethylamineHCID 45078587HCID 45078587, compound

Product 1

HCID 66937230HCID 66937230, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 2,4-dichloro-1H-benzoimidazole (0.550 g, 2.94 mmol) and THF (15 mL) was added DIPEA (1.54 mL, 8.82 mmol) followed by 1-chloromethoxy-2-methoxy-ethane (0.550 g, 4.41 mmol) at 23° C. After stirring for 18 h, EtOAc (100 mL) was added. The organic layer was washed with saturated aqueous NaHCO3 (30 mL) and brine (30 mL). The organic layers were combined, dried, filtered, and concentrated under reduced pressure. The residue was purified (FCC) (10-50% EtOAc/hexanes to yield the titled compound as a mixture of regioisomers (0.660 g, 82%). MS (ESI/CI): mass calcd. for C11H12Cl2N2O2, 274.0; m/z found, 275.1 [M+H]+. 1H NMR (500 MHz, CDCl3): 7.61 (dd, J=8.0, 1.0 Hz, 1H), 7.41 (dd, J=8.1, 0.9 Hz, 1H), 7.33 (dd, J=7.9, 1.0 Hz, 1H), 7.31-7.20 (m, 3H), 5.98 (s, 2H), 5.66 (s, 2H), 3.76-3.69 (m, 2H), 3.67-3.60 (m, 2H), 3.55-3.46 (m, 4H), 3.37 (s, 3H), 3.36 (s, 3H).

Workup

  1. washThe organic layer was washed with saturated aqueous NaHCO3 (30 mL) and brine (30 mL)
  2. customdried
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified (FCC) (10-50% EtOAc/hexanes

Sources & evidence

ORD record
ord-632c2b1865d94ebb9275c8b3e058a023
Source dataset
uspto-grants-2014_06
Patent number
US08759345B2

Reaction notes

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