Hydrazine hydrate (1:1) → HCID 69440052, compound

HRID 404911Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:32]=[CH:31][C:6]([O:7][C:8]2[S:9][C:10]([C:13]3[CH:17]=[C:16]([CH:18]([N:20]4C(=O)C5C(=CC=CC=5)C4=O)[CH3:19])[O:15][N:14]=3)=[CH:11][N:12]=2)=[CH:5][CH:4]=1.O.NN>C(O)C>[CH3:1][O:2][C:3]1[CH:32]=[CH:31][C:6]([O:7][C:8]2[S:9][C:10]([C:13]3[CH:17]=[C:16]([CH:18]([NH2:20])[CH3:19])[O:15][N:14]=3)=[CH:11][N:12]=2)=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of Example 48E (1.06 g, 2.4 mmol) in ethanol (15 mL) was added hydrazine monohydrate (0.698 mL, 144 mmol). The reaction was heated at 60° C. for 45 minutes and then filtered. The filtrate was concentrated and purified by flash chromatography on silica gel eluting with 90:8:2 dichloromethane/methanol/concentrated ammonium hydroxide to provide 746 mg of title compound (98%). 1H NMR (300 MHz, DMSO-d6) δ ppm 1.34 (d, J=6.62 Hz, 3H) 3.80 (s, 3H) 3.99-4.16 (m, 1H) 6.66-6.74 (m, 2H) 6.81-6.85 (m, 1H) 6.99-7.11 (m, 2H) 7.33-7.41 (m, 2H) 7.92 (s, 1H); MS (ESI) m/z 318.0 (M+H)+.

Workup

filtrationfiltered
concentrationThe filtrate was concentrated
custompurified by flash chromatography on silica gel eluting with 90:8:2 dichloromethane/methanol/concentrated ammonium hydroxide

Sources & evidence

ORD record: ord-d2b316aeea27405788b044f62a7fea3c
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08748627B2

Reaction notes

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