Hydrazine hydrate (1:1) → HCID 58031599, compound

HRID 2067629Notes

Reaction equation

O.NN.Cl.NO.C[N:8](C)/[CH:9]=[CH:10]/[C:11]([C:13]1[S:17][C:16]([N:18]2[CH2:22][CH2:21][N:20]([CH2:23][C:24]3[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=3)[C:19]2=[O:34])=[N:15][C:14]=1[CH3:35])=[O:12]>>[O:12]1[C:11]([C:13]2[S:17][C:16]([N:18]3[CH2:22][CH2:21][N:20]([CH2:23][C:24]4[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=4)[C:19]3=[O:34])=[N:15][C:14]=2[CH3:35])=[CH:10][CH:9]=[N:8]1

Participants

Reactant 3

HCID 24654Hydrazine hydrate (1:1)

HCID 443297Hydroxyamine hydrochloride

HCID 58031425HCID 58031425, compound

Product 1

HCID 58031599HCID 58031599, compoundYield 76%

Procedure

Following the procedure as described in Example 38, making variations as required to replace hydrazine monohydrate with hydroxylamine hydrochloride to react with (E)-1-(5-(3-(dimethylamino)acryloyl)-4-methylthiazol-2-yl)-3-(4-(trifluoromethyl)benzyl)imidazolidin-2-one, the title compound was obtained as a colorless solid in 76% yield: mp 153-154° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, CDCl3) δ 8.23 (d, J=1.8 Hz, 1H), 7.67 (d, J=8.1 Hz, 2H), 7.43 (d, J=8.1 Hz, 2H), 6.23 (d, J=1.8 Hz, 1H), 4.53 (s, 2H), 4.17-4.04 (m, 2H), 3.54-3.41 (m, 2H), 2.53 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 163.2, 158.4, 155.5, 150.5, 148.1, 139.7, 128.5, 125.9, 125.8, 122.1, 111.8, 99.4, 47.6, 42.1, 41.9, 17.1; MS (ES+) m/z 409.1 (M+1).

Sources & evidence

ORD record: ord-de8efa77a4bd413aa3e03576833e4477
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08293768B2

Reaction notes

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