Hydrazine hydrate (1:1) → HCID 69435452, compound

HRID 404902Notes

Reaction equation

[Cl:1][C:2]1[CH:31]=[C:30]([O:32][CH2:33][CH:34]2[CH2:36][CH2:35]2)[CH:29]=[CH:28][C:3]=1[O:4][C:5]1[S:6][C:7]([C:10]2[CH:14]=[C:13]([CH:15]([N:17]3C(=O)C4C(=CC=CC=4)C3=O)[CH3:16])[O:12][N:11]=2)=[CH:8][N:9]=1.O.NN>C(O)C>[Cl:1][C:2]1[CH:31]=[C:30]([O:32][CH2:33][CH:34]2[CH2:36][CH2:35]2)[CH:29]=[CH:28][C:3]=1[O:4][C:5]1[S:6][C:7]([C:10]2[CH:14]=[C:13]([CH:15]([NH2:17])[CH3:16])[O:12][N:11]=2)=[CH:8][N:9]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of Example 30G (276 mg, 0.53 mmol) in ethanol (6 mL) was added hydrazine monohydrate (0.16 mL, 3.2 mmol). The reaction was heated at 60° C. for 45 minutes and filtered. The filtrate was concentrated and purified on silica gel eluting with 90:8:2 dichloromethane/methanol/concentrated ammonium hydroxide to provide 201 mg of the title compound (97%) as an amber liquid. 1H NMR (300 MHz, DMSO-d6) δ ppm 0.29-0.38 (m, 2H) 0.53-0.65 (m, 2H) 1.12-1.23 (m, 1H) 1.34 (d, J=7.35 Hz, 3 H) 3.88 (d, J=7.35 Hz, 2H) 3.97-4.15 (m, 1H) 6.84 (s, 1H) 7.03 (dd, J=9.19, 2.94 Hz, 1H) 7.24 (d, J=2.94 Hz, 1H) 7.53 (d, J=9.19 Hz, 1H) 7.91 (s, 1H); MS (ESI) m/z 392.0 (M+H)+.

Workup

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

Sources & evidence

ORD record: ord-07c7a04fe1bc44a994638aed93414193
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08748627B2

Reaction notes

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