(R)-1-Phenyl-3-propanolamine → HCID 118590174, compound

HRID 520225Notes

Reaction equation

HRID 520225 reaction equation
[NH2:1][C@@H:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH2:3][CH2:4][OH:5].[N:12]([C:15]1[CH:20]=[CH:19][C:18]([C:21]2[N:25]=[CH:24][N:23]([C:26]3[CH:31]=[CH:30][C:29]([O:32][C:33]([F:36])([F:35])[F:34])=[CH:28][CH:27]=3)[N:22]=2)=[CH:17][CH:16]=1)=[C:13]=[S:14]>>[OH:5][CH2:4][CH2:3][C@@H:2]([NH:1][C:13]([NH:12][C:15]1[CH:16]=[CH:17][C:18]([C:21]2[N:25]=[CH:24][N:23]([C:26]3[CH:31]=[CH:30][C:29]([O:32][C:33]([F:36])([F:34])[F:35])=[CH:28][CH:27]=3)[N:22]=2)=[CH:19][CH:20]=1)=[S:14])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

3

Reactant 2

HCID 7016858(R)-1-Phenyl-3-propanolamineHCID 1185901653-(4-Isothiocyanatophenyl)-1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazole

Product 1

HCID 118590174HCID 118590174, compound

Procedure

The title compound was prepared with (R)-3-amino-3-phenylpropan-1-ol and 3-(4-isothiocyanato-phenyl)-1-(4-trifluoromethoxy-phenyl)-1H-1,2,4-triazole and isolated as an off-white solid (0.270 g, 64%): mp 162-165° C.; 1H NMR (400 MHz, DMSO-d6) δ 9.74 (s, 1H), 9.37 (d, J=1.8 Hz, 1H), 8.42 (d, J=7.6 Hz, 1H), 8.07-8.01 (m, 4H), 7.63-7.61 (m, 4H), 7.35-7.34 (m, 4H), 7.25-7.26 (m, 1H), 5.58 (s, 1H), 4.65 (s, 1H), 3.39-3.40 (m, 2H), 1.90-2.03 (m, 2H); ESIMS m/z 514 ([M+H]+).

Sources & evidence

ORD record
ord-eeb10a50b5ee481e8ad18d5a6c367840
Source dataset
uspto-grants-2016_05
Patent number
US09326516B2

Reaction notes

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