Hydrochloric Acid → HCID 178442243, compound

HRID 216408Notes

Reaction equation

HRID 216408 reaction equation
Cl.[CH3:2][C:3]([CH3:37])([CH3:36])[CH2:4][C:5]1[N:6]=[C:7]([CH:16]([OH:35])[C:17]2([C:23]3[CH:28]=[CH:27][C:26]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=4)=[CH:25][CH:24]=3)[S:22][CH2:21][CH2:20][CH2:19][S:18]2)[N:8](S(N(C)C)(=O)=O)[CH:9]=1>O1CCCC1>[CH3:2][C:3]([CH3:37])([CH3:36])[CH2:4][C:5]1[N:6]=[C:7]([CH:16]([C:17]2([C:23]3[CH:28]=[CH:27][C:26]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=4)=[CH:25][CH:24]=3)[S:18][CH2:19][CH2:20][CH2:21][S:22]2)[OH:35])[NH:8][CH:9]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86637791HCID 86637791, compound

Product 1

HCID 178442243HCID 178442243, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

Step C, 1.5 N Hydrochloric acid (1 mL) was added to a solution of 4-(2,2-dimethylpropyl)-2-{hydroxy[2-(4-pyridin-2-ylphenyl)-1,3-dithian-2-yl]methyl}-N,N-dimethyl-1H-imidazole-1-sulfonamide in tetrahydrofuran (1 mL). After heating in a sealed tube at 70° C. for a few minutes until no further reaction (LCMS), the reaction mixture was cooled to 0° C., quenched with 10% aqueous sodium hydroxide and extracted with ethyl acetate. The combined organic extracts were dried (magnesium sulfate) and concentrated in vacuo. Preparatory plate chromatography eluting with 10% methanol/ethyl aceate afforded the title compound. LCMS: 440 (M+H).

Workup

  1. temperaturethe reaction mixture was cooled to 0° C.
  2. customquenched with 10% aqueous sodium hydroxide
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic extracts were dried (magnesium sulfate)
  5. concentrationconcentrated in vacuo
  6. washPreparatory plate chromatography eluting with 10% methanol/ethyl aceate

Sources & evidence

ORD record
ord-053bbae116a14252937cbc5c4687260c
Source dataset
uspto-grants-2012_06
Patent number
US08193228B2

Reaction notes

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