Hydrochloric Acid → HCID 58968628, compound

HRID 2075094Notes

Reaction equation

HRID 2075094 reaction equation
[F:1][C:2]([F:48])([F:47])[C:3]1[CH:4]=[C:5]([CH:40]=[C:41]([C:43]([F:46])([F:45])[F:44])[CH:42]=1)[CH2:6][N:7]([CH2:14][C:15]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:17][C:16]=1[C:25]1([O:38][CH3:39])[CH2:30][CH2:29][N:28](C(OC(C)(C)C)=O)[CH2:27][CH2:26]1)[C:8]1[N:9]=[N:10][N:11]([CH3:13])[N:12]=1.Cl>O1CCOCC1>[CH3:39][O:38][C:25]1([C:16]2[CH:17]=[CH:18][C:19]([C:21]([F:24])([F:22])[F:23])=[CH:20][C:15]=2[CH2:14][N:7]([CH2:6][C:5]2[CH:4]=[C:3]([C:2]([F:1])([F:48])[F:47])[CH:42]=[C:41]([C:43]([F:44])([F:45])[F:46])[CH:40]=2)[C:8]2[N:9]=[N:10][N:11]([CH3:13])[N:12]=2)[CH2:26][CH2:27][NH:28][CH2:29][CH2:30]1

Participants

4

Reactant 2

HCID 313Hydrochloric Acid3×HCID 58968624HCID 58968624, compound

Product 1

HCID 58968628HCID 58968628, compoundYield 92.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent4×

Procedure

To a solution of tert-butyl 4-(2-(((3,5-bis(trifluoromethyl)benzyl)(2-methyl-2H-tetrazol-5-yl)amino)methyl)-4-(trifluoromethyl)phenyl)-4-methoxypiperidine-1-carboxylate (321 mg; 0.461 mmol) in 1,4-dioxane (2.5 mL) was added 4.0M hydrogen chloride in 1,4-dioxane (0.5 mL; 2 mmol). The reaction was stirred at room temperature for 2 hours. 4.0M hydrogen chloride in 1,4-dioxane (1.5 mL; 6 mmol) was added and stirred for 1 hour. 4.0M hydrogen chloride in 1,4-dioxane (1.5 mL; 6 mmol) was added and stirred for 1 hour. The solvent was evaporated under reduced pressure. Ethyl acetate was added to the residue and was concentrated under reduced pressure. Isopropyl ether was added and let sit for 16 hours. The solvent was evaporated under reduced pressure to give a white solid. The white solid was triturated with isopropyl ether and filtered off to give 254 mg (87.1% yield) of a white solid. MS (ES+): Calc: 596.4, Found: 597.4 (M+H). 1H NMR (400 MHz, CDCl3) δ ppm 7.92 (s, 2H), 7.87 (s, 1H), 7.59 (d, J=8.30 Hz, 1H), 7.54(d, J=7.88 Hz, 1H), 7.45 (s, 1H), 5.14 (s, 2H), 4.96 (s, 2H), 4.19 (s, 3H), 3.35 (m, 4H), 3.03 (s, 3H), 2.56(d, J=12.86 Hz, 2H), 2.14 (m, 2H).

Workup

  1. stirringstirred for 1 hour
  2. stirringstirred for 1 hour
  3. customThe solvent was evaporated under reduced pressure
  4. additionEthyl acetate was added to the residue
  5. concentrationwas concentrated under reduced pressure
  6. additionIsopropyl ether was added
  7. waitlet sit for 16 hours
  8. customThe solvent was evaporated under reduced pressure
  9. customto give a white solid
  10. customThe white solid was triturated with isopropyl ether
  11. filtrationfiltered off

Sources & evidence

ORD record
ord-b736dcd19fa14e19a5bc6684287e0c66
Source dataset
uspto-grants-2011_04
Patent number
US07919506B2

Reaction notes

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