4-Pyridinemethanamine → 2-(3-(cyclopropylmethyl)-2-oxoimidazolidin-1-yl)-4-methyl-N-(pyridin-4-ylmethyl)thiazole-5-carboxamide

HRID 554993Notes

Reaction equation

HRID 554993 reaction equation
FC1C=C(CN)C=NC=1.[N:10]1[CH:15]=[CH:14][C:13]([CH2:16][NH2:17])=[CH:12][CH:11]=1.[CH:18]1([CH2:21][N:22]2[CH2:26][CH2:25][N:24]([C:27]3[S:28][C:29]([C:33](O)=[O:34])=[C:30]([CH3:32])[N:31]=3)[C:23]2=[O:36])[CH2:20][CH2:19]1>>[CH:18]1([CH2:21][N:22]2[CH2:26][CH2:25][N:24]([C:27]3[S:28][C:29]([C:33]([NH:17][CH2:16][C:13]4[CH:14]=[CH:15][N:10]=[CH:11][CH:12]=4)=[O:34])=[C:30]([CH3:32])[N:31]=3)[C:23]2=[O:36])[CH2:19][CH2:20]1

Participants

4

Reactant 3

HCID 773174-PyridinemethanamineHCID 45116207(5-Fluoropyridin-3-yl)methanamineHCID 579198202-(3-(Cyclopropylmethyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid

Product 1

HCID 579198192-(3-(cyclopropylmethyl)-2-oxoimidazolidin-1-yl)-4-methyl-N-(pyridin-4-ylmethyl)thiazole-5-carboxamideYield 43%

Procedure

Following the procedure as describe in Example 12, making variations as required to replace (5-fluoropyridin-3-yl)methanamine with pyridin-4-ylmethanamine to react with 2-(3-(cyclopropylmethyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid, the title compound was obtained as a colorless solid in 43% yield: mp >200° C. (dichloromethane/hexanes); 1H NMR (300 MHz, CDCl3) δ 8.55-8.53 (m, 2H), 7.23 (d, J=6.0 Hz, 2H), 6.17-6.13 (m, 1H), 4.57 (d, J=6.0 Hz, 2H), 4.14-4.09 (m, 2H), 3.73-3.68 (m, 2H), 3.18 (d, J=7.1 Hz, 2H), 2.62 (s, 3H), 0.99-0.91 (m, 1H), 0.60-0.54 (m, 2H), 0.27-0.22 (m, 2H); 13C NMR (75 MHz, CDCl3) δ 162.8, 157.5, 155.2, 153.9, 149.9, 147.5, 122.2, 116.4, 48.6, 42.6, 42.2, 42.1, 17.3, 8.9, 3.4; MS (ES+) m/z 372.2 (M+1).

Sources & evidence

ORD record
ord-ef61cdd0d0a04815a4ddbc15b04aa19a
Source dataset
uspto-grants-2011_11
Patent number
US08049016B2

Reaction notes

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