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

HRID 560655Notes

Reaction equation

HRID 560655 reaction equation
C(N1CCN(C2SC(C(O)=O)=C(C)N=2)C1=O)C1C=CC=CC=1.[F:23][CH:24]([F:48])[O:25][C:26]1[CH:47]=[CH:46][C:29]([CH2:30][N:31]2[CH2:35][CH2:34][N:33]([C:36]3[S:37][C:38]([C:42]([OH:44])=O)=[C:39]([CH3:41])[N:40]=3)[C:32]2=[O:45])=[CH:28][CH:27]=1.[NH2:49][CH2:50][C:51]1[CH:52]=[N:53][CH:54]=[CH:55][CH:56]=1>>[F:48][CH:24]([F:23])[O:25][C:26]1[CH:27]=[CH:28][C:29]([CH2:30][N:31]2[CH2:35][CH2:34][N:33]([C:36]3[S:37][C:38]([C:42]([NH:49][CH2:50][C:51]4[CH:52]=[N:53][CH:54]=[CH:55][CH:56]=4)=[O:44])=[C:39]([CH3:41])[N:40]=3)[C:32]2=[O:45])=[CH:46][CH:47]=1

Participants

4

Reactant 3

HCID 310183-PyridinemethanamineHCID 579198662-(3-Benzyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acidHCID 594812182-(3-(4-(Difluoromethoxy)benzyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid

Product 1

HCID 250951522-(3-(4-(difluoromethoxy)benzyl)-2-oxoimidazolidin-1-yl)-4-methyl-N-(pyridin-3-ylmethyl)thiazole-5-carboxamideYield 65%

Procedure

Following the procedure as describe in Example 9, making variations as required to replace 2-(3-benzyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid with 2-(3-(4-(difluoromethoxy)benzyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid to react with 3-(aminomethyl)pyridine in place of benzylamine, the title compound was obtained as a white powder in 65% yield: mp 166-167° C.; 1H NMR (300 MHz, CDCl3) δ 8.55-8.40 (m, 3H), 7.67 (d, J=7.8 Hz, 1H), 7.43-6.94 (m, 6H), 4.45-4.35 (m, 4H), 3.97 (t, J=8.1 Hz, 2H), 3.39 (t, J=8.1 Hz, 2H), 2.46 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 162.3, 157.8, 155.5, 151.7, 150.7, 149.3, 148.4, 135.6, 133.8, 130.0, 123.9, 120.1, 119.4, 117.9, 115.0, 46.6, 42.4, 42.0, 40.8, 17.5; MS (ES+) m/z 474.3 (M+1).

Sources & evidence

ORD record
ord-721b9716b4be4bb9bc8b89839fbbe359
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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