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

HRID 560845Notes

Reaction equation

HRID 560845 reaction equation
ClC1C=CC2SC=C(CN3CCN(C4SC(C(O)=O)=C(C)N=4)C3=O)C=2C=1.[CH:27]1([CH2:30][N:31]2[CH2:36][CH2:35][CH2:34][N:33]([C:37]3[S:38][C:39]([C:43]([OH:45])=O)=[C:40]([CH3:42])[N:41]=3)[C:32]2=[O:46])[CH2:29][CH2:28]1.[N:47]1[CH:52]=[CH:51][CH:50]=[C:49]([CH2:53][NH2:54])[CH:48]=1>>[CH:27]1([CH2:30][N:31]2[CH2:36][CH2:35][CH2:34][N:33]([C:37]3[S:38][C:39]([C:43]([NH:54][CH2:53][C:49]4[CH:48]=[N:47][CH:52]=[CH:51][CH:50]=4)=[O:45])=[C:40]([CH3:42])[N:41]=3)[C:32]2=[O:46])[CH2:28][CH2:29]1

Participants

4

Reactant 3

HCID 310183-PyridinemethanamineHCID 580314002-(3-(cyclopropylmethyl)-2-oxotetrahydropyrimidin-1(2H)-yl)-4-methylthiazole-5-carboxylic acidHCID 580315052-(3-((5-Chlorobenzo[b]thiophen-3-yl)methyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid

Product 1

HCID 594812282-(3-(cyclopropylmethyl)-2-oxotetrahydropyrimidin-1(2H)-yl)-4-methyl-N-(pyridin-3-ylmethyl)thiazole-5-carboxamideYield 22%

Procedure

Following the procedure as described in Example 32, making variations as required to replace 2-(3-((5-chlorobenzo[b]thiophen-3-yl)methyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid with 2-(3-(cyclopropylmethyl)-2-oxotetrahydro pyrimidin-1(2H)-yl)-4-methylthiazole-5-carboxylic acid to react with pyridin-3-ylmethanamine, the title compound was obtained as a colorless solid in 22% yield: nip 142-145° C. (dichloromethane/hexanes); 1H NMR (300 MHz, CDCl3) δ 8.57 (s, 1H), 8.52-8.51 (m, 1H), 7.68-7.65 (m, 1H), 7.28-7.23 (m, 1H), 6.07 (m, 1H), 4.56 (d, J=5.8 Hz, 2H), 4.15 (t, J=5.9 Hz, 2H), 3.48 (t, J=5.9 Hz, 2H), 3.31 (d, J=7.0 Hz, 2H), 2.61 (s, 3H), 2.16-2.09 (m, 2H), 1.05-0.98 (m, 1H), 0.55-0.49 (m, 2H), 0.28-0.23 (m, 2H); 13C NMR (75 MHz, CDCl3) δ 163.0, 159.2, 152.9, 152.7, 149.0, 148.6, 135.6, 133.9, 123.6, 117.6, 52.8, 45.6, 45.5, 41.2, 21.3, 17.3, 9.3, 3.4; MS (ES+) m/z 386.2 (M+1).

Sources & evidence

ORD record
ord-19e98ae432a64c1091462ed622c0f87f
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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