4-Fluoroaniline → HCID 59481241, compound

HRID 560865Notes

Reaction equation

FC1C=CC(CN)=CC=1.[F:10][C:11]1[CH:17]=[CH:16][C:14]([NH2:15])=[CH:13][CH:12]=1.CS(O[CH2:23][CH2:24][N:25]1[C:29](=[O:30])[N:28]([C:31]2[S:32][C:33]([C:37](=[O:46])[NH:38][CH2:39][C:40]3[CH:41]=[N:42][CH:43]=[CH:44][CH:45]=3)=[C:34]([CH3:36])[N:35]=2)[CH:27]=[N:26]1)(=O)=O>>[F:10][C:11]1[CH:17]=[CH:16][C:14]([NH:15][CH2:23][CH2:24][N:25]2[C:29](=[O:30])[N:28]([C:31]3[S:32][C:33]([C:37]([NH:38][CH2:39][C:40]4[CH:41]=[N:42][CH:43]=[CH:44][CH:45]=4)=[O:46])=[C:34]([CH3:36])[N:35]=3)[CH:27]=[N:26]2)=[CH:13][CH:12]=1

Participants

Reactant 3

HCID 97314-Fluoroaniline

HCID 673264-Fluorobenzylamine

HCID 594812642-(4-(4-methyl-5-(pyridin-3-ylmethylcarbamoyl)thiazol-2-yl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)ethyl methanesulfonate

Product 1

HCID 59481241HCID 59481241, compoundYield 66%

Procedure

Following the procedure as described in Example 47, making variations as required to replace (4-fluorophenyl)methanamine with 4-fluoroaniline to react with 2-(4-(4-methyl-5-(pyridin-3-ylmethylcarbamoyl)thiazol-2-yl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)ethyl methanesulfonate, the title compound was obtained as a colorless solid in 66% yield: mp 163-164° C. (ethyl acetate/hexane); 1H MNR (300 MHz, CDCl3) δ 8.56 (br s, 1H), 8.51-8.41 (m, 1H), 8.22 (s, 1H), 7.71-7.62 (m, 1H), 7.23-7.19 (m, 1H), 6.91-6.75 (m, 3H), 6.54-6.47 (m, 2H), 4.57 (d, J=5.8 Hz, 2H), 4.09-3.92 (m, 3H), 3.53-3.39 (m, 2H), 2.61 (s, 3H); MS (ES+) m/z 454.1 (M+1).

Sources & evidence

ORD record: ord-23e93307cbcd4706a22d2d71ce8c445e
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08063084B2

Reaction notes

Loading…