Hydrochloric Acid → HCID 178490669, compound

HRID 2196811Notes

Reaction equation

HRID 2196811 reaction equation
[C:1]([C:5]1[S:9]/[C:8](=[N:10]\[C:11](=[O:21])[C:12]2[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=2[O:19][CH3:20])/[N:7]([CH2:22][C@@H:23]2[CH2:27][CH2:26][CH2:25][N:24]2C(OC(C)(C)C)=O)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].Cl.O1CCOCC1>CO>[C:1]([C:5]1[S:9]/[C:8](=[N:10]\[C:11](=[O:21])[C:12]2[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=2[O:19][CH3:20])/[N:7]([CH2:22][C@@H:23]2[CH2:27][CH2:26][CH2:25][NH:24]2)[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 178490670HCID 178490670, compound

Product 1

HCID 178490669HCID 178490669, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of Example 29B (140 mg, 0.28 mmol.) in methanol (2 mL) was added hydrogen chloride in dioxane (0.5 mL, 2.000 mmol) and stirred for 12 hr. The solvent was removed under reduced pressure and the residue recrystallized from methanol:diethyl ether to provide the title compound as a hydrogen chloride salt. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.33 (s, 9 H) 1.68-1.79 (m, 1 H) 1.87-2.01 (m, 2 H) 2.03-2.12 (m, 1 H) 3.14-3.28 (m, 2 H) 3.81 (s, 3 H) 3.93-4.06 (m, 1 H) 4.47 (d, J=6.44 Hz, 2 H) 7.14 (d, J=9.16 Hz, 1 H) 7.45-7.50 (m, 2 H) 7.63 (d, J=2.71 Hz, 1 H) 9.29 (d, J=4.41 Hz, 2 H); MS (DCI) m/z 408 (M+H)+. Anal. calcd for C20H26ClN3O2S.2HCl.1.0H2O: C, 48.15; H, 6.06; N, 8.42. Found: C, 48.00; H, 6.04; N, 8.27.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue recrystallized from methanol

Sources & evidence

ORD record
ord-1961d894ca534e2c9646f92a141296aa
Source dataset
uspto-grants-2012_12
Patent number
US08338467B2

Reaction notes

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