Hydrazine hydrate (1:1) → HCID 178433089, compound

HRID 1882445Notes

Reaction equation

[C:1]([C:4]1[S:8][C:7]([N:9]2[CH2:13][CH2:12][N:11]([CH2:14][CH:15]3[CH2:17][CH2:16]3)[C:10]2=[O:18])=[N:6][C:5]=1[CH3:19])(=O)[CH3:2].COC(OC)[N:23]([CH3:25])C.O.[NH2:29]N>CN(C)C=O>[CH:15]1([CH2:14][N:11]2[CH2:12][CH2:13][N:9]([C:7]3[S:8][C:4]([C:1]4[CH:2]=[CH:25][NH:23][N:29]=4)=[C:5]([CH3:19])[N:6]=3)[C:10]2=[O:18])[CH2:17][CH2:16]1

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of 1-(5-acetyl-4-methylthiazol-2-yl)-3-(cyclopropylmethyl)-imidazolidin-2-one (0.24 g, 0.85 mmol) in N,N-dimethylformamide (10 mL) was added N,N-dimethylformamide dimethyl acetal (0.20 mL, 1.50 mmol). The reaction mixture was heated for 17 hours at 110° C., followed by the addition of hydrazine monohydrate (0.20 mL, 4.11 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 and the title compound was obtained as a white solid in 76% yield (0.20 g): mp 169-171° C. (ethyl acetate); 1H NMR (300 MHz, DMSO-d6) δ 12.8 (s, 1H), 7.74 (br s, 1H), 6.40 (d, J=3.0 Hz, 1H), 3.98-3.92 (m, 2H), 3.62-3.57 (m, 2H), 3.05 (d, J=7.2 Hz, 2H), 2.36 (s, 3H), 0.95-0.84 (m, 1H), 0.49-0.43 (m, 2H), 0.21-0.17 (m, 2H); 1H NMR (75 MHz, DMSO-d6) δ 156.0, 155.5, 142.5, 103.3, 48.2, 42.5, 42.4, 16.9, 9.3, 3.6; MS (ES+) m/z 304.2 (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-2a0379b4dae84bb3bb2f594670c2caf9
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08318949B2

Reaction notes

Loading…