1-Cyclopropylethanamine → HCID 54742334, compound

HRID 1887273Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[CH:6][N:5]([C:8]2[S:9][C:10]([C:14]([OH:16])=O)=[C:11]([CH3:13])[N:12]=2)[C:4](=[O:17])[CH:3]=1.[CH:18]1([CH:21]([NH2:23])C)[CH2:20][CH2:19]1>>[CH:18]1([CH2:21][NH:23][C:14]([C:10]2[S:9][C:8]([N:5]3[CH:6]=[CH:7][C:2]([OH:1])=[CH:3][C:4]3=[O:17])=[N:12][C:11]=2[CH3:13])=[O:16])[CH2:20][CH2:19]1

Participants

Reactant 2

HCID 5192391-Cyclopropylethanamine

HCID 547423412-(4-hydroxy-2-oxopyridin-1(2H)-yl)-4-methylthiazole-5-carboxylic acid

Product 1

HCID 54742334HCID 54742334, compoundYield 76%

Procedure

Following the procedure as described in Example 1, making variations only as required to use 2-(4-hydroxy-2-oxopyridin-1(2H)-yl)-4-methylthiazole-5-carboxylic acid in place of 4-methyl-2-(2-oxo-4-phenylpyridin-1(2H)-yl)thiazole-5-carboxylic acid to react with cyclopropylethanamine, the title compound was obtained as a colorless solid in 76% yield: mp 240-242° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, DMSO-d6) δ 11.56 (br s, 1H), 8.58 (d, J=8.0 Hz, 1H), 8.26 (t, J=5.6 Hz, 1H), 6.25 (dd, J=8.0, 2.5 Hz, 1H), 5.81 (d, J=2.5 Hz, 1H), 3.05 (m, 2H), 2.51 (s, 3H), 1.05-0.92 (m, 1H), 0.43-0.36 (m, 2H), 0.20-0.15 (m, 2H); 13C NMR (75 MHz, DMSO-d6) δ 167.9, 161.8, 161.6, 153.9, 149.7, 132.6, 124.0, 104.3, 98.0, 43.9, 17.4, 11.4, 3.7; MS (ES+) m/z: 306.2 (M+1).

Sources & evidence

ORD record: ord-a761c1c87c9d4b8683fbe2dd929da5c7
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501746B2

Reaction notes

Loading…