Methanol → HCID 58147264, compound

HRID 508567Notes

Reaction equation

HRID 508567 reaction equation
O1C=CC([C:6]2S[C:9]([S:11]([N:14]3[CH2:23][CH2:22][C:21]4[C:16](=[CH:17][CH:18]=[C:19]([C:24]([O:26]C)=O)[CH:20]=4)[CH2:15]3)(=[O:13])=[O:12])=[CH:8][CH:7]=2)=N1.CO.Cl.[NH2:31][OH:32].[OH-].[K+]>CS(C)=O>[CH2:9]([S:11]([N:14]1[CH2:23][CH2:22][C:21]2[C:16](=[CH:17][CH:18]=[C:19]([C:24]([NH:31][OH:32])=[O:26])[CH:20]=2)[CH2:15]1)(=[O:12])=[O:13])[CH2:8][CH2:7][CH3:6]

Participants

6

Reactant 4

HCID 887MethanolHCID 14797Potassium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 66970161HCID 66970161, compound

Product 1

HCID 58147264HCID 58147264, compoundYield 6.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of methyl 2-[(5-isoxazol-3-yl-2-thienyl)sulfonyl]-1,2,3,4-tetrahydroisoquinoline-6-carboxylate obtained in step 1 in methanol (2 mL, 50 mmol) was added hydroxylamine hydrochloride (80 mg, 1 mmol) and potassium hydroxide (200 mg, 4 mmol). The reaction was left to stir for 2 hours at 80° C. Upon cooling to room temperature the solvent was removed in vacuo. The residue obtained was dissolved in DMSO (1 mL), the residual solids were removed by filtration and the resulting residue following evaporation was purified via reverse phase prep HPLC to afford the title compound as a white solid after lyophilization (Yield: 6.1%). LCMS (FA) ES+ 313; 1H NMR (400 MHz, d6 DMSO) δ: 0.87 (t, J=7.32, 7.46 Hz, 3H), 1.38 (q, J=7.545, 7.25, 7.57 Hz, 2H), 1.63 (q, J=7.76, 7.55, 7.80 Hz, 2H), 2.91 (t, J=5.29, 6.47 Hz, 2H), 4.44 (s, J=8.06, 7.81 Hz, 2H), 3.49 (t, 2H, 6.03 Hz, J=5.95), 4.44 (s, 2H), 7.24 (d, J=7.5 Hz, 1H), 7.56 (d, J=8.1 Hz, 1H), and 7.58 (s, 1H).

Workup

  1. waitThe reaction was left
  2. temperatureUpon cooling to room temperature the solvent
  3. customwas removed in vacuo
  4. customThe residue obtained
  5. customthe residual solids were removed by filtration
  6. customevaporation
  7. customwas purified via reverse phase prep HPLC

Sources & evidence

ORD record
ord-6208f9f0abe247c28ab289e8bcdcedcc
Source dataset
uspto-grants-2015_08
Patent number
US09096518B2

Reaction notes

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