Hydrazine hydrate (1:1) → HCID 178433092, compound

HRID 554977Notes

Reaction equation

[C:1]([C:4]1[S:8][C:7]([N:9]2[CH2:13][CH2:12][N:11]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)[C:10]2=[O:22])=[N:6][C:5]=1[CH3:23])(=O)[CH3:2].COC(OC)[N:27]([CH3:29])C.O.[NH2:33]N>CN(C)C=O>[F:21][C:18]1[CH:19]=[CH:20][C: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:29][NH:27][N:33]=4)=[C:5]([CH3:23])[N:6]=3)[C:10]2=[O:22])=[CH:16][CH:17]=1

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of 1-(5-acetyl-4-methylthiazol-2-yl)-3-(4-fluorobenzyl)-imidazolidin-2-one (0.33 g, 1.00 mmol) in N,N-dimethylformamide (10 mL) was added N,N-dimethylformamide dimethyl acetal (0.25 mL, 1.88 mmol). The reaction mixture was heated for 7 hours at 110° C., followed by the addition of hydrazine monohydrate (0.30 mL, 6.18 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 in 61% yield (0.22 g): mp 239-242° C. (ethyl acetate); 1H NMR (300 MHz, DMSO-d6) δ 12.90 (br s, 1H), 7.76 (br s, 1H), 7.35-7.31 (m, 2H), 7.19-7.13 (m, 2H), 6.42 (d, J=2.1 Hz, 1H), 4.39 (s, 2H), 3.98-3.93 (m, 2H), 3.44-3.38 (m, 2H), 2.36 (s, 3H), 2.24 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ 163.6, 160.4, 155.7, 144.0, 142.5, 133.2, 130.4, 118.1, 116.0, 115.7, 103.2, 46.6, 42.4, 42.0, 16.9; MS (ES+) m/z 358.2 (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-67911171ad0f4bca975ff4203c5ca91d
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08049016B2

Reaction notes

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