Hydrochloric Acid → HCID 178442442, compound

HRID 1881487Notes

Reaction equation

HRID 1881487 reaction equation
Cl.CN(C)S([N:7]1[CH:11]=[C:10]([CH2:12][C:13]([CH3:17])([CH3:16])[CH2:14][CH3:15])[N:9]=[C:8]1[CH:18]([NH:43][C:44](=[O:46])[CH3:45])[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([N:26]2[CH2:31][CH2:30][CH2:29][C:28]3[CH:32]=[N:33][N:34](COCC[Si](C)(C)C)[C:27]2=3)=[CH:22][CH:21]=1)(=O)=O>CO>[CH3:16][C:13]([CH3:17])([CH2:14][CH3:15])[CH2:12][C:10]1[N:9]=[C:8]([CH:18]([NH:43][C:44](=[O:46])[CH3:45])[CH2:19][C:20]2[CH:21]=[CH:22][C:23]([N:26]3[CH2:31][CH2:30][CH2:29][C:28]4[CH:32]=[N:33][NH:34][C:27]3=4)=[CH:24][CH:25]=2)[NH:7][CH:11]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66705746N-{1-[1-[(dimethylamino)sulfonyl]-4-(2,2-dimethylbutyl)-1H-imidazol-2-yl]-2-[4-(1-{[2-(trimethylsilyl)ethoxy]methyl}-1,4,5,6-tetrahydro-7H-pyrazolo[3,4-b]pyridin-7-yl)phenyl]ethyl}acetamide

Product 1

HCID 178442442HCID 178442442, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

Hydrogen chloride (4 M in 1,4-dioxane) (1 mL, 4 mmol) was added to an ambient temperature solution of N-{1-[1-[(dimethylamino)sulfonyl]-4-(2,2-dimethylbutyl)-1H-imidazol-2-yl]-2-[4-(1-{[2-(trimethylsilyl)ethoxy]methyl}-1,4,5,6-tetrahydro-7H-pyrazolo[3,4-b]pyridin-7-yl)phenyl]ethyl}acetamide (30 mg, 0.04 mmol) in methanol (3 mL). After stirring at 70° C. for 1 h, volatiles were removed. 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. High pressure liquid chromatography (KR100-5C18 100×21.2 mm column) eluting with 10-100% acetonitrile/water containing 0.05% trifluoroacetic acid afforded the title compound. (M+H) found: 435.

Workup

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

Sources & evidence

ORD record
ord-08a7a9f696184c98a4a83a76b1895dfa
Source dataset
uspto-grants-2012_11
Patent number
US08318767B2

Reaction notes

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