Hydrochloric Acid → HCID 178445741, compound

HRID 1036450Notes

Reaction equation

HRID 1036450 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, 1H), 7.93 (d, J=9.2 Hz, 1H), 7.91 (d, J=1.9 Hz, 1H), 7.81 (dd, J=2.1, 9.3 Hz, 1H), 7.33 (d, J=9.2 Hz, 1H), 5.06 (d, J=6.5 Hz, 2H), 4.82 (d, J=6.5 Hz, 2H), 4.38-4.24 (m, 1H), 2.20 (d, J=12.4 Hz, 2H), 1.93-1.82 (m, 2H), 1.55 (br. s., 2H), 1.41-1.09 (m, 5H), 0.89 (s, 9H).

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-244e7fea00484fd1ba83d26704cb1794
Source dataset
uspto-grants-2013_10
Patent number
US08546359B2

Reaction notes

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