Hydrochloric Acid → 2-(2-(4-chlorophenyl)oxazol-4-yl)-2-methyl-N-(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)propan-1-amine hydrochloride

HRID 1397412Notes

Reaction equation

HRID 1397412 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[O:7][N:6]=[C:5]([C:8]2[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=2)[CH:11]=O)[N:4]=1.[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[O:26][CH:27]=[C:28]([C:30]([CH3:34])([CH3:33])[CH2:31][NH2:32])[N:29]=2)=[CH:21][CH:20]=1.[ClH:35]>O1CCOCC1>[Cl:18][C:19]1[CH:20]=[CH:21][C:22]([C:25]2[O:26][CH:27]=[C:28]([C:30]([CH3:34])([CH3:33])[CH2:31][NH:32][CH2:11][C:10]3[CH:13]=[CH:14][CH:15]=[C:8]([C:5]4[N:4]=[C:3]([C:2]([F:17])([F:16])[F:1])[O:7][N:6]=4)[CH:9]=3)[N:29]=2)=[CH:23][CH:24]=1.[ClH:35].[Cl:18][C:19]1[CH:20]=[CH:21][C:22]([C:25]2[O:26][CH:27]=[C:28]([C:30]([CH3:34])([CH3:33])[CH2:31][NH:32][CH2:11][C:10]3[CH:13]=[CH:14][CH:15]=[C:8]([C:5]4[N:4]=[C:3]([C:2]([F:17])([F:16])[F:1])[O:7][N:6]=4)[CH:9]=3)[N:29]=2)=[CH:23][CH:24]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 185454733-(5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzaldehydeHCID 673256232-(2-(4-Chlorophenyl)oxazol-4-yl)-2-methylpropan-1-amine

Product 2

HCID 712804192-(2-(4-Chlorophenyl)oxazol-4-yl)-2-methyl-N-(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)propan-1-amineHCID 712806732-(2-(4-chlorophenyl)oxazol-4-yl)-2-methyl-N-(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)propan-1-amine hydrochlorideYield 6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2-(2-(4-Chlorophenyl)oxazol-4-yl)-2-methyl-N-(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)propan-1-amine was synthesized from 3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzaldehyde and 2-(2-(4-chlorophenyl)oxazol-4-yl)-2-methylpropan-1-amine as described in example 7 step 3. The free amine was then treated with HCl in dioxane (2 M) at 0° C. and stirred at room temperature for 30 min. The reaction mixture was concentrated under reduced pressure. The crude was purified by washing with dry hexane to get 2-(2-(4-chlorophenyl)oxazol-4-yl)-2-methyl-N-(3-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)propan-1-amine hydrochloride (20 mg, yield 6%). 1H NMR (400 MHz, DMSO-d6) δ 8.87 (br s, 2H), 8.26 (s, 1H), 8.11-8.08 (m, 2H), 7.85-7.80 (m, 3H), 7.69-7.65 (t, J=7.6 Hz, 1H), 7.55-7.52 (d, J=8.5 Hz, 2H), 4.28 (br s, 2H), 3.12 (m, 2H), 1.33 (s, 6H). MS (ESI) m/z: Calculated for C23H20ClF3N4O2: 476.12. found: 477.2 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customThe crude was purified
  3. washby washing with dry hexane

Sources & evidence

ORD record
ord-becd6915f1324eb58bf5da22b7a3e260
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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