Hydrazine hydrate (1:1) → HCID 178485330, compound

HRID 560857Notes

Reaction equation

HRID 560857 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:46]=[C:47]([CH:52]=[CH:53][CH:54]=3)[C:48]([NH:50][CH3:51])=[O:49])[C:40]2=[O:55])=[N:36][C:35]=1[CH3:56])(=O)[CH3:32].COC(OC)([N:61](C)C)C.O.NN>>[CH3:51][NH:50][C:48](=[O:49])[C:47]1[CH:52]=[CH:53][CH:54]=[C:45]([CH2:44][N:41]2[CH2:42][CH2:43][N:39]([C:37]3[S:38][C:34]([C:31]4[NH:61][N:6]=[C:5]([CH3:4])[CH:32]=4)=[C:35]([CH3:56])[N:36]=3)[C:40]2=[O:55])[CH:46]=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 580313943-((3-(5-acetyl-4-methylthiazol-2-yl)-2-oxoimidazolidin-1-yl)methyl)-N-methylbenzamide

Product 1

HCID 178485330HCID 178485330, compoundYield 54%

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 3-((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 54% yield: nip 259-261° C. (ethyl acetate); 1H NMR (300 MHz, DMSO-d6) δ 7.73-7.62 (m, 2H), 7.42-7.34 (m, 2H), 6.32 (br s, 1H), 4.51 (s, 2H), 4.13-4.04 (m, 2H), 3.49-3.41 (m, 2H), 2.97 (d, J=4.8 Hz, 3H), 2.60 (s, 3 H), 2.45 (s, 3H); MS (ES+) m/z 373.1 (M+1).

Sources & evidence

ORD record
ord-d6428f1dba9b48a088de1e959e0a6784
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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