(R)-beta-aminophenethyl alcohol → HCID 118590132, compound

HRID 520220Notes

Reaction equation

HRID 520220 reaction equation
[NH2:1][C@H:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:3][OH:4].[N:11]([C:14]1[CH:19]=[CH:18][C:17]([C:20]2[N:24]=[CH:23][N:22]([C:25]3[CH:30]=[CH:29][C:28]([O:31][C:32]([F:35])([F:34])[F:33])=[CH:27][CH:26]=3)[N:21]=2)=[CH:16][CH:15]=1)=[C:12]=[S:13]>>[OH:4][CH2:3][C@H:2]([NH:1][C:12]([NH:11][C:14]1[CH:15]=[CH:16][C:17]([C:20]2[N:24]=[CH:23][N:22]([C:25]3[CH:30]=[CH:29][C:28]([O:31][C:32]([F:35])([F:33])[F:34])=[CH:27][CH:26]=3)[N:21]=2)=[CH:18][CH:19]=1)=[S:13])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

3

Reactant 2

HCID 2724025(R)-beta-aminophenethyl alcoholHCID 1185901653-(4-Isothiocyanatophenyl)-1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazole

Product 1

HCID 118590132HCID 118590132, compound

Procedure

The title compound was prepared with (R)-2-amino-2-phenylethanol and 3-(4-isothiocyanato-phenyl)-1-(4-trifluoromethoxy-phenyl)-1H-1,2,4-triazole (Lambert, W.; et al., WO 2011017513) and isolated as an off-white solid (0.285 g, 69%): mp 98-101° C.; 1H NMR (400 MHz, DMSO-d6) δ 9.99 (s, 1H), 9.37 (s, 1H), 8.40 (d, J=7.9 Hz, 1H), 8.07-8.01 (m, 4H), 7.73 (d, J=7.7 Hz, 2H), 7.61 (d, J=8.5 Hz, 2H), 7.38-7.24 (m, 5H), 5.42 (s, 1H), 5.12 (s, 1H), 3.73 (s, 2H); ESIMS m/z 500 ([M+H]+).

Sources & evidence

ORD record
ord-436704df4dfa47b6af24f57fdeeeae50
Source dataset
uspto-grants-2016_05
Patent number
US09326516B2

Reaction notes

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