Hydrazine hydrate (1:1) → HCID 58031547, compound

HRID 560851Notes

Reaction equation

HRID 560851 reaction equation
C[N:2](C)/C=C/C(C1SC(N2CCN(CC3C=CC(C(F)(F)F)=CC=3)C2=O)=NC=1C)=O.C[N:32](C)/[C:33](/[CH3:60])=[CH:34]/[C:35]([C:37]1[S:41][C:40]([N:42]2[CH2:46][CH2:45][N:44]([CH2:47][C:48]3[CH:53]=[CH:52][C:51]([C:54]([F:57])([F:56])[F:55])=[CH:50][CH:49]=3)[C:43]2=[O:58])=[N:39][C:38]=1[CH3:59])=O.O.NN>>[CH3:59][C:38]1[N:39]=[C:40]([N:42]2[CH2:46][CH2:45][N:44]([CH2:47][C:48]3[CH:49]=[CH:50][C:51]([C:54]([F:56])([F:55])[F:57])=[CH:52][CH:53]=3)[C:43]2=[O:58])[S:41][C:37]=1[C:35]1[CH:34]=[C:33]([CH3:60])[NH:32][N:2]=1

Participants

4

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 58031425HCID 58031425, compoundHCID 58031507HCID 58031507, compound

Product 1

HCID 58031547HCID 58031547, compoundYield 67%

Procedure

Following the procedure as described in Example 38, making variations as required to replace (E)-1-(5-(3-(dimethylamino)acryloyl)-4-methylthiazol-2-yl)-3-(4-(trifluoromethyl)benzyl)imidazolidin-2-one with (E)-1-(5-(3-(dimethylamino)but-2-enoyl)-4-methylthiazol-2-yl)-3-(4-(trifluoromethyl)benzyl)imidazolidin-2-one to react with hydrazine monohydrate, the title compound was obtained as a colorless solid in 67% yield: mp 238-239° C. (ethyl acetate); 1H NMR (300 MHz, CDCl3) δ 7.53 (d, J=7.8 Hz, 2H), 7.34 (d, J=7.8 Hz, 2H), 6.08 (s 1H), 4.52 (s, 2H), 4.04-3.99 (m, 2 H), 3.42-3.36 (m, 2H), 2.36 (s, 3H), 2.24 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 156.8, 155.8, 143.1, 139.9, 130.3, 129.9, 128.3, 125.8, 125.7, 122.1, 103.6, 47.5, 41.9, 41.8, 16.0, 10.8; MS (ES+) m/z 422.1 (M+1).

Sources & evidence

ORD record
ord-16a05e87a47343018fe5fee044787138
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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