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

HRID 573947Notes

Reaction equation

HRID 573947 reaction equation
O[C@@H]([C@H](O)C(O)=O)C(O)=O.[F:11][C:12]([F:36])([F:35])[O:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]2[CH:24]=[N:23][C:22]([C:25]3[CH:30]=[CH:29][C:28]([CH2:31][C@H:32]([NH2:34])[CH3:33])=[CH:27][CH:26]=3)=[N:21]2)=[CH:16][CH:15]=1>CO>[F:36][C:12]([F:11])([F:35])[O:13][C:14]1[CH:15]=[CH:16][C:17]([N:20]2[CH:24]=[N:23][C:22]([C:25]3[CH:30]=[CH:29][C:28]([CH2:31][C@H:32]([NH2:34])[CH3:33])=[CH:27][CH:26]=3)=[N:21]2)=[CH:18][CH:19]=1

Participants

3

Reactant 1

HCID 131732840(R)-1-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)propan-2-amine (2S,3S)-2,3-dihydroxysuccinate

Product 1

HCID 90412523(R)-1-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)propan-2-amineYield 89.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(R)-1-(4-(1-(4-(Trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)propan-2-amine(2S,3S)-2,3-dihydroxysuccinate (CB59) (0.35 g, 0.68 mmol) was slurried in methanol (20 mL) and SCX silica gel (2 g). The solution was stirred for 3 hours, filtered, and washed with methanol (20 mL). The compound was eluted from the SCX silica gel using ammonium hydroxide (5% in MeOH, 25 mL). The filtrate was concentrated providing the title compound as a white solid (0.22 g, 87%): mp 84-88° C.; 1H NMR (400 MHz, CDCl3) d 8.56 (s, 1H), 8.13 (d, J=8.2 Hz, 2H), 7.80 (d, J=9.0 Hz, 2H), 7.44 7.35 (m, 2H), 7.31 (d, J=8.1 Hz, 2H), 3.29 3.15 (m, 1H), 2.78 (dd, J=13.2, 5.4 Hz, 1H), 2.60 (dd, J=13.2, 8.0 Hz, 1H), 1.49 (s, 2H), 1.15 (d, J=6.3 Hz, 3H).

Workup

  1. filtrationfiltered
  2. washwashed with methanol (20 mL)
  3. washThe compound was eluted from the SCX silica gel
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-638fa50146b540bcbbb9de55cba54db7
Source dataset
uspto-grants-2015_05
Patent number
US09029560B2

Reaction notes

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