3-Pyridinemethanamine → HCID 57744468, compound

HRID 1887280Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([C:15]2[S:19][C:18]([C:20](O)=[O:21])=[C:17]([CH3:23])[CH:16]=2)[C:11](=[O:24])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:25][CH2:26][C:27]1[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=1>>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([C:15]2[S:19][C:18]([C:20]([NH:25][CH2:26][C:27]3[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=3)=[O:21])=[C:17]([CH3:23])[CH:16]=2)[C:11](=[O:24])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Reactant 2

HCID 310183-Pyridinemethanamine

HCID 57744504HCID 57744504, compound

Product 1

HCID 57744468HCID 57744468, compoundYield 39%

Procedure

Following the procedure as described in Example 1, making variations only as required to use 5-(4-(benzyloxy)-2-oxopyridin-1(2H)-yl)-3-methylthiophene-2-carboxylic acid in place of 4-methyl-2-(2-oxo-4-phenylpyridin-1(2H)-yl)thiazole-5-carboxylic acid to react with 3-(aminomethyl)pyridine, the title compound was obtained as a colorless solid in 39% yield: mp 165-167° C.; 1H NMR (300 MHz, CDCl3) δ 8.61 (d, J=1.5 Hz, 1H), 8.54 (dd, J=4.7, 1.5 Hz, 1H), 7.71 (dt, J=7.8, 1.5 Hz, 1H), 7.57 (d, J=7.8 Hz, 1H), 7.43-7.27 (m, 6H), 6.85 (s, 1H), 6.30 (t, J=5.8 Hz, 1H), 6.15 (dd, J=7.8, 2.7 Hz, 1H), 6.06 (d, J=2.7 Hz, 1H), 5.04 (s, 2H), 4.61 (d, J=5.8 Hz, 2H), 2.54 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ 166.2, 162.6, 160.9, 138.8, 137.5, 135.4, 135.0, 128.5, 128.2, 128.0, 126.9, 120.5, 102.6, 97.3, 70.0, 15.5; MS (ES+) m/z 432.2 (M+1).

Sources & evidence

ORD record: ord-541c2b5e2fc04207941909787ebd1fb7
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501746B2

Reaction notes

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