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

HRID 554991Notes

Reaction equation

HRID 554991 reaction equation
FC1C=C(CN)C=NC=1.[N:10]1[CH:15]=[CH:14][CH:13]=[N:12][C:11]=1[CH2:16][NH2:17].[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:11]4[N:12]=[CH:13][CH:14]=[CH:15][N:10]=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 46580472-PyrimidinemethanamineHCID 45116207(5-Fluoropyridin-3-yl)methanamineHCID 579198202-(3-(Cyclopropylmethyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid

Product 1

HCID 579197452-(3-(cyclopropylmethyl)-2-oxoimidazolidin-1-yl)-4-methyl-N-(pyrimidin-2-ylmethyl)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 pyrimidin-2-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 58% yield: mp 218-220° C. (dichloromethane/hexanes); 1H NMR (300 MHz, CDCl3) δ 8.71 (d, J=4.9 Hz, 2H), 7.24-7.21 (m, 1H), 7.15-7.11 (m, 1H), 4.83 (d, J=4.4 Hz, 2H), 4.16-4.11 (m, 2H), 3.74-3.68 (m, 2H), 3.20 (d, J=7.1 Hz, 2H), 2.66 (s, 3H), 1.01-0.91 (m, 1H), 0.59-0.54 (m, 2H), 0.28-0.25 (m, 2H); 13C NMR (75 MHz, CDCl3) δ 165.4, 162.5, 157.7, 157.1, 155.2, 152.7, 119.5, 117.6, 48.6, 45.5, 42.2, 42.1, 17.2, 8.9, 3.4; MS (ES+) m/z 373.3 (M+1).

Sources & evidence

ORD record
ord-5baa826000e740ed943dfe95e0fb1b07
Source dataset
uspto-grants-2011_11
Patent number
US08049016B2

Reaction notes

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