Hydrazine hydrate (1:1) → HCID 178433093, compound

HRID 554976Notes

Reaction equation

[C:1]([C:4]1[S:8][C:7]([N:9]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH:16]3[CH2:18][CH2:17]3)[C:10]2=[O:19])=[N:6][C:5]=1[CH3:20])(=O)[CH3:2].COC(OC)[N:24]([CH3:26])C.O.[NH2:30]N>CN(C)C=O>[CH:16]1([CH2:15][CH2:14][N:11]2[CH2:12][CH2:13][N:9]([C:7]3[S:8][C:4]([C:1]4[CH:2]=[CH:26][NH:24][N:30]=4)=[C:5]([CH3:20])[N:6]=3)[C:10]2=[O:19])[CH2:18][CH2:17]1

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of 1-(5-acetyl-4-methylthiazol-2-yl)-3-(2-cyclopropylethyl) imidazolidin-2-one (0.30 g, 1.00 mmol) in N,N-dimethylformamide (10 mL) was added N,N-dimethylformamide dimethyl acetal (0.30 mL, 2.25 mmol). The reaction mixture was heated for 23 hours at 110° C., followed by the addition of hydrazine monohydrate (0.30 mL, 6.16 mmol). The reaction mixture was heated for another 10 minutes at 110° C., and concentrated in vacuo. The residue was washed with water and triturated with ethyl acetate to afford the title compound as a white solid in 71% yield (0.23 g): mp 147-149° C. (ethyl acetate); 1H NMR (300 MHz, DMSO-d6) δ 7.77-7.75 (m, 1H), 6.40 (d, J=1.2 Hz, 1H), 4.00-3.94 (m, 2H), 3.58-3.549 (m, 2H), 3.25 (t, J=6.9 Hz, 2H), 2.36 (s, 3H), 1.46-1.34 (m, 2H), 0.89-0.81 (m, 1H), 0.69-0.64 (m, 2H), 0.05-0.02 (m, 2H); 13C NMR (75 MHz, DMSO-d6) δ 156.0, 155.5, 144.1, 142.3, 130.2, 117.9, 103.1, 43.8, 42.4, 42.3, 32.1, 16.9, 8.8, 4.5; MS (ES+) m/z 318.2 (M+1).

Workup

temperatureThe reaction mixture was heated for another 10 minutes at 110° C.
concentrationconcentrated in vacuo
washThe residue was washed with water
customtriturated with ethyl acetate

Sources & evidence

ORD record: ord-2f5cf911afb042b18622fcc6ea0d6284
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08049016B2

Reaction notes

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