Cyclopentanethiol → HCID 178517608, compound

HRID 589990Notes

Reaction equation

HRID 589990 reaction equation
[CH:1]1([SH:6])[CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].CS([C:13]1[S:14][C:15]([C:30]2[CH:34]=[CH:33][NH:32][N:31]=2)=[C:16]2[CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[C:18](=[O:29])[C:17]=12)(=O)=O>C1COCC1>[CH:1]1([S:6][C:13]2[S:14][C:15]([C:30]3[CH:34]=[CH:33][NH:32][N:31]=3)=[C:16]3[CH2:21][CH2:20][NH:19][C:18](=[O:29])[C:17]=23)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 15510CyclopentanethiolHCID 24758Sodium hydrideHCID 178451569HCID 178451569, compound

Product 1

HCID 178517608HCID 178517608, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of cyclopentanethiol (54 μL, 0.50 mmol) in THF (0.5 mL) at 0° C. was added NaH (20.0 mg, 0.50 mmol). The reaction mixture was warmed to rt and tert-butyl 3-(methylsulfonyl)-4-oxo-1-(1H-pyrazol-3-yl)-6,7-dihydrothieno[3,4-c]pyridine-5(4H)-carboxylate (100 mg, 0.25 mmol) was added, After 30 min, the reaction was quenched with aqueous NH4Cl and extracted with CH2Cl2. The combined extracts were dried (Na2SO4) and concentrated. Purification by silica gel chromatography (gradient elution, 0-100% EtOAc /hexanes) afforded the title compound. 1H NMR (400 MHz, ppm, CD3OD) δ 7.73 (d, J=2.3 Hz, 1 H); 6.50 (d, J=2.4 Hz, 1 H); 3.77 (m, 1 H); 3.44 (t, J=6.2 Hz, 2 H); 3.04 (t, J=6.3 Hz, 2 H); 2.32-2.22 (m, 2 H); 1.85-1.77 (m, 2 H); 1.76-1.65 (m, 4 H). HRMS (ES+) m/z 320.0879 [(M+H)+; calcd for C15 H17N3OS2: 320.0886].

Workup

  1. customthe reaction was quenched with aqueous NH4Cl
  2. extractionextracted with CH2Cl2
  3. dry with materialThe combined extracts were dried (Na2SO4)
  4. concentrationconcentrated
  5. customPurification
  6. washby silica gel chromatography (gradient elution, 0-100% EtOAc /hexanes)

Sources & evidence

ORD record
ord-e238f0bd05ae422eb80fb49fc441f630
Source dataset
uspto-grants-2016_01
Patent number
US09233977B2

Reaction notes

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