Tetrahydrofuran → HCID 1251121, compound

HRID 1616698Notes

Reaction equation

HRID 1616698 reaction equation
[NH2:1][C:2]1[S:12][C:5]2[CH2:6][O:7][C:8]([CH3:11])([CH3:10])[CH2:9][C:4]=2[C:3]=1[C:13]([O:15][CH3:16])=[O:14].[CH2:17]1[CH2:21][O:20][CH2:19][CH2:18]1>>[C:19]([NH:1][C:2](=[S:12])[NH:1][C:2]1[S:12][C:5]2[CH2:6][O:7][C:8]([CH3:11])([CH3:10])[CH2:9][C:4]=2[C:3]=1[C:13]([O:15][CH3:16])=[O:14])(=[O:20])[C:18]1[CH:17]=[CH:21][CH:13]=[CH:3][CH:4]=1

Participants

3

Reactant 2

HCID 8028TetrahydrofuranHCID 974814HCID 974814, compound

Product 1

HCID 1251121HCID 1251121, compoundYield 72%

Conditions

Temperature
50 °C

Procedure

To a combined mixture of methyl 2-amino-5,5-dimethyl-5,7-dihydro-4H-thieno[2,3-c]pyran-3-carboxylate (ChemBridge, CAS 713111-73-0, 31 mg, 0.13 mmol, 1 equiv.) and PhCONCS (0.02 mL, 0.15 mmol, 1.2 equiv.) was added THF (0.7 mL) The resulting solution was stirred at 50° C. for 3 days. The solvent was then removed under reduced pressure and the crude product was triturated with hexanes, filtered, and rinsed with hexanes (4×5 mL). The product was further purified by preparatory HPLC (0-50% EtOAC:hexanes) and isolated as a white solid (38 mg, 72% yield). 1H NMR (400 MHz, CDCl3) δ 14.83 (s, 1H), 9.14 (s, 1H), 7.98 (dd, J=8.4, 1.2 Hz, 2H), 7.72-7.63 (m, 1H), 7.56 (dd, J=10.5, 4.8 Hz, 2H), 4.77 (t, J=1.5 Hz, 2H), 4.04 (s, 3H), 2.85 (s, 2H), 1.35 (s, 6H). LCMS retention time: 3.508 min; LCMS purity at 215 nm=96%. HRMS m/z calculated for C19H21N2O4S2 [M++1]: 405.0937. found 405.0942.

Workup

  1. customThe solvent was then removed under reduced pressure
  2. customthe crude product was triturated with hexanes
  3. filtrationfiltered
  4. washrinsed with hexanes (4×5 mL)
  5. customThe product was further purified by preparatory HPLC (0-50% EtOAC:hexanes)

Sources & evidence

ORD record
ord-0730cef8624643b19aa31eeba052df8a
Source dataset
uspto-grants-2014_07
Patent number
US08765803B1

Reaction notes

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