Hydrazine hydrate (1:1) → HCID 66954115, compound

Participants

Reaction Steps

The product of Example 9.3 (17 mg, 0.036 mmol) was treated with TFA/water (9:1 v/v, 1 mL). After 5 min the mixture was evaporated in vacuo. The residue was redissolved in methanolic ammonia (7M, 4 mL) and Pd-black (17 mg, 0.16 mmol) was added, followed by hydrazine hydrate (250 μL, 5.1 mmol). After 15 min more Pd-black (22 mg, 0.21 mmol) was added and again after further 15 min (55 mg, 0.52 mmol) and also hydrazine hydrate (0.5 mL, 10.2 mmol). Shortly after the mixture was filtered through flux calcined diatomaceous earth and evaporated. The residue was dissolved in MeOH (2 mL) and treated with Amberlyst® A-26(OH) ion exchange resin (˜1 g) for 5 min, the solution was filtered and evaporated in vacuo which gave the product as an oil (7 mg, 62%). 1H NMR (CD3OD) δ 8.16 (s, 1H), 7.48 (s, 1H), 3.97-3.80 (m, 2H), 3.79-3.61 (m, 2H), 3.16-3.05 (m, 1H), 2.85 (dd, J=6.0, 12.1, 1H), 2.79 (dd, J=6.7, 12.0 Hz, 1H), 2.66 (dd, J=4.8, 13.5 Hz, 1H), 2.56 (dd, J=8.0, 13.5 Hz, 1H), 2.11-1.88 (m, 4H). 13C NMR (CD3OD, referenced to the middle methanol peak at 49.0 ppm) δ 150.8, 146.5, 129.1, 114.6, 72.1, 62.1, 45.5, 43.9, 40.1, 16.3. HRMS: (M+H)+ calcd. for C13H22N5O2S: 312.1494. found: 312.1494.

Provenance & Evidence