Hydrazine hydrate (1:1) → HCID 178485432, compound

HRID 2067635Notes

Reaction equation

HRID 2067635 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]([C:21]([N:23]4CCCC[CH2:24]4)=[O:22])=[CH:17][CH:16]=3)[C:10]2=[O:29])=[N:6][C:5]=1[CH3:30])(=O)C.C([C:34]1SC(N2CCN(CC3C=CC(C(NC)=O)=CC=3)C2=O)=[N:36][C:35]=1[CH3:56])(=O)C.COC(OC)([N:61](C)C)C.O.NN>>[CH3:24][NH:23][C:21](=[O:22])[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[NH:61][N:36]=[C:35]([CH3:56])[CH:34]=4)=[C:5]([CH3:30])[N:6]=3)[C:10]2=[O:29])=[CH:16][CH:17]=1

Participants

5

Reactant 4

HCID 24654Hydrazine hydrate (1:1)HCID 878351,1-Dimethoxyethyl(dimethyl)amineHCID 580313851-(5-Acetyl-4-methylthiazol-2-yl)-3-(4-(piperidine-1-carbonyl)benzyl)imidazolidin-2-oneHCID 580315834-((3-(5-acetyl-4-methylthiazol-2-yl)-2-oxoimidazolidin-1-yl)methyl)-N-methylbenzamide

Product 1

HCID 178485432HCID 178485432, compoundYield 80%

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 4-((3-(5-acetyl-4-methylthiazol-2-yl)-2-oxoimidazolidin-1-yl)methyl)-N-methylbenzamide to react with N,N-dimethylacetamide dimethyl acetal and further with hydrazine monohydrate, the title compound was obtained as a colorless solid in 80% yield: mp 236-238° C. (ethyl acetate); 1H NMR (300 MHz, DMSO-d6) δ 8.40 (d, J=4.2 Hz, 1H), 7.79 (d, J=8.1 Hz, 2H), 7.35 (d, J=8.1 Hz, 2H), 6.16 (s, 1H), 4.44 (s, 2H), 4.03-3.93 (m, 2H), 3.45-3.40 (m, 2H), 2.67 (d, J=4.2 Hz, 3H), 2.34 (s, 3H), 2.22 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ 166.7, 155.8, 144.0, 142.3, 140.1, 134.1, 128.0, 127.8, 102.7, 102.6, 47.1, 42.4, 42.3, 42.2, 26.7, 16.9; MS (ES+) m/z 411.1 (M+1).

Sources & evidence

ORD record
ord-a5fe0c1eaa1147abb25798f941d2d932
Source dataset
uspto-grants-2012_10
Patent number
US08293768B2

Reaction notes

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