L-Tartaric acid → (S)-1-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)propan-2-amine (2R,3R)-2,3-dihydroxysuccinate

HRID 573946Notes

Reaction equation

HRID 573946 reaction equation
[F:1][C:2]([F:26])([F:25])[O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:14]=[N:13][C:12]([C:15]3[CH:20]=[CH:19][C:18]([CH2:21][CH:22]([NH2:24])[CH3:23])=[CH:17][CH:16]=3)=[N:11]2)=[CH:6][CH:5]=1.[OH:27][C@H:28]([C@@H:32]([OH:36])[C:33]([OH:35])=[O:34])[C:29]([OH:31])=[O:30]>>[OH:27][C@H:28]([C@@H:32]([OH:36])[C:33]([OH:35])=[O:34])[C:29]([OH:31])=[O:30].[F:26][C:2]([F:1])([F:25])[O:3][C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH:14]=[N:13][C:12]([C:15]3[CH:20]=[CH:19][C:18]([CH2:21][C@@H:22]([NH2:24])[CH3:23])=[CH:17][CH:16]=3)=[N:11]2)=[CH:8][CH:9]=1

Participants

3

Reactant 2

HCID 444305L-Tartaric acidHCID 904118321-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)propan-2-amine

Product 1

HCID 131732841(S)-1-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)propan-2-amine (2R,3R)-2,3-dihydroxysuccinate

Procedure

The title compound was prepared as described in Example 99 using 1-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)propan-2-amine (CB58) and (2R,3R)-2,3-dihydroxysuccinic acid and isolated as a white solid (0.70 g, 49%): mp 187-191° C.; 1H NMR 1H NMR (400 MHz, DMSO-d6) δ 9.40 (s, 1H), 8.08 (dd, J=8.6, 3.6 Hz, 4H), 7.63 (dt, J=8.1, 1.0 Hz, 2H), 7.49 7.32 (m, 2H), 3.81 (s, 2H), 3.47 (dt, J=8.5, 6.2 Hz, 1H), 3.01 (dd, J=13.4, 5.5 Hz, 1H), 2.74 (dd, J=13.4, 8.7 Hz, 1H), 1.13 (d, J=6.4 Hz, 3H) (OH and NH2 not observed).

Sources & evidence

ORD record
ord-52a1ca1331114688ab5dc6737e01b627
Source dataset
uspto-grants-2015_05
Patent number
US09029560B2

Reaction notes

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