Hydrochloric Acid → HCID 178445741, compound

HRID 2389111Notes

Reaction equation

HRID 2389111 reaction equation
[C:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]([O:11][C:12]2[C:13]([C:33]([F:36])([F:35])[F:34])=[C:14]3[C:19](=[CH:20][CH:21]=2)[CH:18]=[C:17]([C:22]2([NH:26]S(C(C)(C)C)=O)[CH2:25][O:24][CH2:23]2)[CH:16]=[CH:15]3)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].C(Cl)Cl.Cl.CCOCC>C1CCCCC1>[C:1]([C@H:5]1[CH2:6][CH2:7][C@H:8]([O:11][C:12]2[C:13]([C:33]([F:36])([F:34])[F:35])=[C:14]3[C:19](=[CH:20][CH:21]=2)[CH:18]=[C:17]([C:22]2([NH2:26])[CH2:23][O:24][CH2:25]2)[CH:16]=[CH:15]3)[CH2:9][CH2:10]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 6344DichloromethaneHCID 178455557HCID 178455557, compound

Product 1

HCID 178445741HCID 178445741, compoundYield 80.2%

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

To a solution of 2-methyl-propane-2-sulfinic acid {3-[6-(trans-4-tert-butyl-cyclohexyloxy)-5-trifluoromethyl-naphthalen-2-yl]-oxetan-3-yl}-amide (332 mg, 0.632 mmol) in methylene chloride (7 mL, 100 mmol) was added 2.0 M of hydrogen chloride in ether (0.632 mL, 1.26 mmol) and stirred for 10 min. A precipitate formed and cyclohexane was added to dilute the mixture. After removal of solvent, the residue was dissolved in methylene chloride, 1M aq. NH4OH was added, the extracted organic layer was dried and subjected to silica gel chromatography with MeOH/CH2Cl2 (20-40%) to give 3-(6-(trans-4-tert-butylcyclohexyloxy)-5-(trifluoromethyl)naphthalen-2-yl)oxetan-3-amine as a solid (213.7 mg, 80%). LCMS: Rf=1.67 min 405.20 ([M-16]). 1H NMR (400 MHz, CHLOROFORM-d) δ=8.27 (d, J=9.3 Hz, 1 H), 7.93 (d, J=9.2 Hz, 1 H), 7.91 (d, J=1.9 Hz, 1 H), 7.81 (dd, J=2.1, 9.3 Hz, 1 H), 7.33 (d, J=9.2 Hz, 1 H), 5.06 (d, J=6.5 Hz, 2 H), 4.82 (d, J=6.5 Hz, 2 H), 4.38-4.24 (m, 1 H), 2.20 (d, J=12.4 Hz, 2 H), 1.93-1.82 (m, 2 H), 1.55 (br. s., 2 H), 1.41-1.09 (m, 5 H), 0.89 (s, 9 H).

Workup

  1. customA precipitate formed
  2. additionto dilute the mixture
  3. customAfter removal of solvent
  4. dissolutionthe residue was dissolved in methylene chloride
  5. addition1M aq. NH4OH was added
  6. customthe extracted organic layer was dried

Sources & evidence

ORD record
ord-ba058bb8ee4241be90553a97162bafff
Source dataset
uspto-grants-2012_09
Patent number
US08269043B2

Reaction notes

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