Pyrimidin-4-ylmethanamine → 2-(3-(cyclopropylmethyl)-2-oxoimidazolidin-1-yl)-4-methyl-N-(pyrimidin-4-ylmethyl)thiazole-5-carboxamide

HRID 554990Notes

Reaction equation

HRID 554990 reaction equation
FC1C=C(CN)C=NC=1.[N:10]1[CH:15]=[CH:14][C:13]([CH2:16][NH2:17])=[N: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][N: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 12933348Pyrimidin-4-ylmethanamineHCID 45116207(5-Fluoropyridin-3-yl)methanamineHCID 579198202-(3-(Cyclopropylmethyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid

Product 1

HCID 579197832-(3-(cyclopropylmethyl)-2-oxoimidazolidin-1-yl)-4-methyl-N-(pyrimidin-4-ylmethyl)thiazole-5-carboxamideYield 65%

Procedure

Following the procedure as describe in Example 12, making variations as required to replace (5-fluoropyridin-3-yl)methanamine with pyrimidin-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 65% yield: mp 188-191° C. (dichloromethane/hexanes); 1H NMR (300 MHz, CDCl3) δ 9.17 (s, 1H), 8.68 (d, J=5.1 Hz, 1H), 7.33 (d, J=4.9 Hz, 1H), 6.89-6.87 (m, 1H), 4.69 (d, J=5.0 Hz, 2H), 4.16-4.11 (m, 2H), 3.74-3.69 (m, 2H), 3.20 (d, J=7.1 Hz, 2H), 2.64 (s, 3H), 1.00-0.91 (m, 1H), 0.61-0.55 (m, 2H), 0.28-0.23 (m, 2H); 13C NMR (75 MHz, CDCl3) δ 165.0, 162.8, 158.5, 157.9, 156.9, 155.2, 153.2, 119.1, 117.1, 48.6, 44.1, 42.2, 42.1, 17.3, 8.9, 3.5; MS (ES+) m/z 373.2 (M+1).

Sources & evidence

ORD record
ord-6acfbef2edf6441a9ef27a702a22158c
Source dataset
uspto-grants-2011_11
Patent number
US08049016B2

Reaction notes

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