(5-Fluoropyridin-3-yl)methanamine → 2-(3-isobutyl-2-oxoimidazolidin-1-yl)-4-methyl-N-((6-methylpyrazin-2-yl)methyl)thiazole-5-carboxamide

HRID 555000Notes

Reaction equation

HRID 555000 reaction equation
FC1C=C(CN)C=NC=1.[CH3:10][C:11]1[N:16]=[C:15]([CH2:17][NH2:18])[CH:14]=[N:13][CH:12]=1.[CH2:19]([N:23]1[CH2:27][CH2:26][N:25]([C:28]2[S:29][C:30]([C:34](O)=[O:35])=[C:31]([CH3:33])[N:32]=2)[C:24]1=[O:37])[CH:20]([CH3:22])[CH3:21]>>[CH2:19]([N:23]1[CH2:27][CH2:26][N:25]([C:28]2[S:29][C:30]([C:34]([NH:18][CH2:17][C:15]3[CH:14]=[N:13][CH:12]=[C:11]([CH3:10])[N:16]=3)=[O:35])=[C:31]([CH3:33])[N:32]=2)[C:24]1=[O:37])[CH:20]([CH3:22])[CH3:21]

Participants

4

Reactant 3

HCID 45116207(5-Fluoropyridin-3-yl)methanamineHCID 579199962-(3-Isobutyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acidHCID 666611366-Methyl-2-pyrazinemethanamine

Product 1

HCID 579197902-(3-isobutyl-2-oxoimidazolidin-1-yl)-4-methyl-N-((6-methylpyrazin-2-yl)methyl)thiazole-5-carboxamideYield 46%

Procedure

Following the procedure as describe in Example 12, making variations as required to replace (5-fluoropyridin-3-yl)methanamine with (6-methylpyrazin-2-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 46% yield: mp 139-142° C. (dichloromethane/hexanes); 1H NMR (300 MHz, CDCl3) δ 8.50 (s, 1H), 8.38 (s, 1H), 6.75-6.72 (m, 1H), 4.69 (d, J=5.0 Hz, 2H), 4.14-4.08 (m, 2H), 3.62-3.56 (m, 2H), 3.13 (d, J=7.4 Hz, 2H), 2.62 (s, 3H), 2.56 (s, 3H), 1.98-1.88 (m, 1H), 0.94 (d, J=6.6 Hz, 6H); 13C NMR (75 MHz, CDCl3) δ 162.6, 157.7, 155.7, 153.1, 152.5, 148.7, 143.4, 142.7, 117.1, 51.5, 42.9, 42.3, 42.0, 26.8, 21.2, 19.9, 17.2; MS (ES+) m/z 388.8 (M+1).

Sources & evidence

ORD record
ord-f1ebd55b0a504ce4ac80c43197e9c3e4
Source dataset
uspto-grants-2011_11
Patent number
US08049016B2

Reaction notes

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