Hydrazine hydrate (1:1) → 1-(4-fluorobenzyl)-3-(4-methyl-5-(5-methyl-1H-pyrazol-3-yl)thiazol-2-yl)imidazolidin-2-one

HRID 560855Notes

Reaction equation

HRID 560855 reaction equation
C([C:4]1SC(N2CCN(CC3C=CC(C(N4CCCCC4)=O)=CC=3)C2=O)=[N:6][C:5]=1C)(=O)C.[C:31]([C:34]1[S:38][C:37]([N:39]2[CH2:43][CH2:42][N:41]([CH2:44][C:45]3[CH:50]=[CH:49][C:48]([F:51])=[CH:47][CH:46]=3)[C:40]2=[O:52])=[N:36][C:35]=1[CH3:53])(=O)[CH3:32].COC(OC)([N:58](C)C)C.O.NN>>[F:51][C:48]1[CH:49]=[CH:50][C:45]([CH2:44][N:41]2[CH2:42][CH2:43][N:39]([C:37]3[S:38][C:34]([C:31]4[CH:32]=[C:5]([CH3:4])[NH:6][N:58]=4)=[C:35]([CH3:53])[N:36]=3)[C:40]2=[O:52])=[CH:46][CH:47]=1

Participants

5

Reactant 4

HCID 24654Hydrazine hydrate (1:1)HCID 878351,1-Dimethoxyethyl(dimethyl)amineHCID 579197651-(5-Acetyl-4-methylthiazol-2-yl)-3-(4-fluorobenzyl)imidazolidin-2-oneHCID 580313851-(5-Acetyl-4-methylthiazol-2-yl)-3-(4-(piperidine-1-carbonyl)benzyl)imidazolidin-2-one

Product 1

HCID 579197511-(4-fluorobenzyl)-3-(4-methyl-5-(5-methyl-1H-pyrazol-3-yl)thiazol-2-yl)imidazolidin-2-oneYield 46%

Procedure

Following the procedure as described in Example 40, making variations as required to replace 1-(5-acetyl-4-methylthiazol-2-yl)-3-(4-(piperidine-1-carbonyl)benzyl)imidazolidin-2-one with 1-(5-acetyl-4-methylthiazol-2-yl)-3-(4-fluorobenzyl)imidazolidin-2-one to react with N,N-dimethylacetamide dimethyl acetal and further with hydrazine monohydrate, the title compound was obtained as a colorless solid in 46% yield: mp 218-221° C. (ethyl acetate); 1H NMR (300 MHz, CDCl3) δ 7.28-7.23 (m, 2H), 7.05-6.97 (m, 2H), 6.15 (s, 1H), 4.44 (s, 2H), 4.09-4.02 (m, 2H), 3.43-3.38 (m, 2H), 2.52 (s, 3H), 2.24 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 164.1, 160.8, 156.5, 155.7, 143.4, 131.7, 130.1, 129.9, 115.8, 115.6, 103.7, 47.3, 42.0, 41.7, 16.5, 11.4; MS (ES+) m/z 372.2 (M+1).

Sources & evidence

ORD record
ord-2f522b6693534eb39569e38b1408d576
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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