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

HRID 555002Notes

Reaction equation

HRID 555002 reaction equation
FC1C=C(CN)C=NC=1.[CH3:10][N:11]1[CH:15]=[CH:14][C:13]([CH2:16][NH2:17])=[N:12]1.[CH2:18]([N:22]1[CH2:26][CH2:25][N:24]([C:27]2[S:28][C:29]([C:33](O)=[O:34])=[C:30]([CH3:32])[N:31]=2)[C:23]1=[O:36])[CH:19]([CH3:21])[CH3:20]>>[CH2:18]([N:22]1[CH2:26][CH2:25][N:24]([C:27]2[S:28][C:29]([C:33]([NH:17][CH2:16][C:13]3[CH:14]=[CH:15][N:11]([CH3:10])[N:12]=3)=[O:34])=[C:30]([CH3:32])[N:31]=2)[C:23]1=[O:36])[CH:19]([CH3:21])[CH3:20]

Participants

4

Reactant 3

HCID 7019419(1-Methylpyrazol-3-yl)methanamineHCID 45116207(5-Fluoropyridin-3-yl)methanamineHCID 579199962-(3-Isobutyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid

Product 1

HCID 579198932-(3-isobutyl-2-oxoimidazolidin-1-yl)-4-methyl-N-((1-methyl-1H-pyrazol-3-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-3-yl)methanamine 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 158-161° C. (dichloromethane/hexanes); 1H NMR (300 MHz, CDCl3) δ 7.43 (s, 1H), 7.37 (s, 1H), 5.80-5.78 (m, 1H), 4.39 (d, J=5.3 Hz, 2H), 4.12-4.07 (m, 2H), 3.86 (s, 3H), 3.60-3.55 (m, 2H), 3.11 (d, J=7.4 Hz, 2H), 2.59 (s, 3H), 1.96-1.87 (m, 1H), 0.93 (d, J=7.4 Hz, 6H); 13C NMR (75 MHz, CDCl3) δ 162.4, 157.4, 155.6, 152.9 152.6, 138.6, 129.5, 118.3, 117.0, 51.5, 42.8, 41.9, 38.8, 34.3, 26.7, 19.9, 17.1; MS (ES+) m/z 376.8 (M+1).

Sources & evidence

ORD record
ord-de2f6c31870c48b89f569cb98d8fba98
Source dataset
uspto-grants-2011_11
Patent number
US08049016B2

Reaction notes

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