1,4-Dimethylpyrazole → 2-(3-isobutyl-2-oxoimidazolidin-1-yl)-4-methyl-N-((1-methyl-1H-pyrazol-4-yl)methyl)thiazole-5-carboxamide

HRID 1882472Notes

Reaction equation

HRID 1882472 reaction equation
FC1C=C(CN)C=[N:6]C=1.[CH3:10][N:11]1[CH:15]=[C:14]([CH3:16])[CH:13]=[N:12]1.[CH2:17]([N:21]1[CH2:25][CH2:24][N:23]([C:26]2[S:27][C:28]([C:32](O)=[O:33])=[C:29]([CH3:31])[N:30]=2)[C:22]1=[O:35])[CH:18]([CH3:20])[CH3:19]>>[CH2:17]([N:21]1[CH2:25][CH2:24][N:23]([C:26]2[S:27][C:28]([C:32]([NH:6][CH2:16][C:14]3[CH:13]=[N:12][N:11]([CH3:10])[CH:15]=3)=[O:33])=[C:29]([CH3:31])[N:30]=2)[C:22]1=[O:35])[CH:18]([CH3:20])[CH3:19]

Participants

4

Reactant 3

HCID 1368361,4-DimethylpyrazoleHCID 45116207(5-Fluoropyridin-3-yl)methanamineHCID 579199962-(3-Isobutyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid

Product 1

HCID 579198752-(3-isobutyl-2-oxoimidazolidin-1-yl)-4-methyl-N-((1-methyl-1H-pyrazol-4-yl)methyl)thiazole-5-carboxamideYield 58%

Procedure

Following the procedure as describe in Example 12, making variations as required to replace (5-fluoropyridin-3-yl)methanamine with (1-methyl-1H-pyrazol-4-yl)methane to react with 2-(3-isobutyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid in place of 2-(3-(cyclopropylmethyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid, the title compound was obtained as a colorless solid in 58% yield: mp 155-158° C. (dichloromethane/hexanes); 1H NMR (300 MHz, CDCl3) δ 7.43 (s, 1H), 7.37 (s, 1H), 5.80-5.77 (m, 1H), 4.39 (d, J=5.3 Hz, 2H), 4.12-4.07 (m, 2H), 3.87 (s, 3H), 3.60-3.55 (m, 2H), 3.11 (d, J=7.4 Hz, 2H), 2.60 (s, 3H), 1.96-1.87 (m, 1H), 0.93 (d, J=7.4 Hz, 6H); 13C NMR (75 MHz, CDCl3) δ 162.3, 157.4, 155.6, 152.8 152.6, 138.6, 129.4, 118.3, 117.0, 51.5, 42.8, 41.9, 38.8, 34.3, 26.7, 19.9, 17.1; MS (ES+) m/z 377.1 (M+1).

Sources & evidence

ORD record
ord-b2b229d4c81e4bb4994113da90bc71b9
Source dataset
uspto-grants-2012_11
Patent number
US08318949B2

Reaction notes

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