2-Pyridinemethanamine → HCID 25094875, compound

HRID 2067413Notes

Reaction equation

FC1C=CC(CN)=CC=1.[NH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1.[CH2:18]([N:25]1[CH2:29][CH2:28][N:27]([C:30]2[S:31][C:32]([C:36](O)=[O:37])=[C:33]([CH3:35])[N:34]=2)[C:26]1=[O:39])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>>[CH2:18]([N:25]1[CH2:29][CH2:28][N:27]([C:30]2[S:31][C:32]([C:36]([NH:10][CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=3)=[O:37])=[C:33]([CH3:35])[N:34]=2)[C:26]1=[O:39])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

Reactant 3

HCID 195092-Pyridinemethanamine

HCID 673264-Fluorobenzylamine

HCID 579198662-(3-Benzyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid

Product 1

HCID 25094875HCID 25094875, compoundYield 43%

Procedure

Following the procedure as describe in Example 9, making variations as required to replace 4-fluorobenzylamine with 2-(aminomethyl)pyridine to react with 2-(3-benzyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid, the title compound was obtained as a white powder in 43% yield: mp 149-151° C.; 1H NMR (300 MHz, DMSO-d6) δ 8.52-8.46 (m, 2H), 7.72 (t, J=5.7 Hz, 1H), 7.39-7.19 (m, 7H), 4.49 (d, J=5.7 Hz, 2H), 4.40 (s, 2H), 3.97 (t, J=7.5 Hz, 2H), 3.42 (t, J=7.5 Hz, 2H), 2.46 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ 162.4, 159.1, 157.9, 155.5, 151.5, 149.2, 137.1, 136.7, 129.1, 128.2, 127.9, 122.4, 121.2, 118.2, 47.3, 45.0, 42.4, 42.0, 17.6; MS (ES+) m/z 408.3 (M+1).

Sources & evidence

ORD record: ord-e074abf85b0d413db82b35566799c929
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08293768B2

Reaction notes

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