Hydrochloric Acid → HCID 178480058, compound

HRID 425366Notes

Reaction equation

HRID 425366 reaction equation
Cl.CN(C)S([N:7]1[CH:11]=[C:10]([CH2:12][C:13]([CH3:16])([CH3:15])[CH3:14])[N:9]=[C:8]1[C:17]([OH:40])([CH3:39])[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[C:26]([NH:31]C(=O)OC(C)(C)C)=[N:27][N:28]([CH3:30])[CH:29]=2)=[CH:21][CH:20]=1)(=O)=O>CO>[NH2:31][C:26]1[C:25]([C:22]2[CH:23]=[CH:24][C:19]([CH2:18][C:17]([C:8]3[NH:7][CH:11]=[C:10]([CH2:12][C:13]([CH3:16])([CH3:15])[CH3:14])[N:9]=3)([OH:40])[CH3:39])=[CH:20][CH:21]=2)=[CH:29][N:28]([CH3:30])[N:27]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86637793tert-butyl [4-(4-{2-[1-[(dimethylamino)sulfonyl]-4-(2,2-dimethylpropyl)-1H-imidazo 1-2-yl]-2-hydroxypropyl}phenyl)-1-methyl-1H-pyrazol-3-yl]carbamate

Product 1

HCID 178480058HCID 178480058, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

Hydrogen chloride (4 M in 1,4-dioxane) (2 μL, 8 mmol) was added to an ambient temperature solution of tert-butyl [4-(4-{2-[1-[(dimethylamino)sulfonyl]-4-(2,2-dimethylpropyl)-1H-imidazo 1-2-yl]-2-hydroxypropyl}phenyl)-1-methyl-1H-pyrazol-3-yl]carbamate (33 mg, 0.06 mmol) in methanol (2 mL). After stirring at 70° C. for 1 h, volatiles were removed. The residue was purified with high pressure liquid chromatography (KR100-5C18 100×21.2 mm column) eluting with 10-100% acetonitrile/water containing 0.05% trifluoroacetic acid. The residue was partitioned between methanol/ethyl acetate and 10% aqueous sodium hydroxide. The aqueous phase was extracted with ethyl acetate. The combined organic extracts were dried (magnesium sulfate) and concentrated in vacuo to afford the title compound. (M+H) found: 368.

Workup

  1. customvolatiles were removed
  2. customThe residue was purified with high pressure liquid chromatography (KR100-5C18 100×21.2 mm column)
  3. washeluting with 10-100% acetonitrile/water containing 0.05% trifluoroacetic acid
  4. customThe residue was partitioned between methanol/ethyl acetate and 10% aqueous sodium hydroxide
  5. extractionThe aqueous phase was extracted with ethyl acetate
  6. dry with materialThe combined organic extracts were dried (magnesium sulfate)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bd71133fbf4c4b0888bfdfe75222f8fe
Source dataset
uspto-grants-2012_01
Patent number
US08106070B2

Reaction notes

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