Hydrochloric Acid → HCID 178442238, compound

HRID 425363Notes

Reaction equation

HRID 425363 reaction equation
Cl.[CH3:2][C:3]([CH3:44])([CH3:43])[CH2:4][C:5]1[N:6]=[C:7]([C:16]([OH:42])([CH3:41])[CH2:17][C:18]2[CH:23]=[CH:22][C:21]([N:24]3[CH2:29][CH2:28][CH2:27][C:26]4[CH:30]=[N:31][N:32](COCC[Si](C)(C)C)[C:25]3=4)=[CH:20][CH:19]=2)[N:8](S(N(C)C)(=O)=O)[CH:9]=1>CO>[CH3:2][C:3]([CH3:44])([CH3:43])[CH2:4][C:5]1[N:6]=[C:7]([C:16]([OH:42])([CH3:41])[CH2:17][C:18]2[CH:19]=[CH:20][C:21]([N:24]3[CH2:29][CH2:28][CH2:27][C:26]4[CH:30]=[N:31][NH:32][C:25]3=4)=[CH:22][CH:23]=2)[NH:8][CH:9]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 667056964-(2,2-dimethylpropyl)-2-{1-hydroxy-1-methyl-2-[4-(1-{[2-(trimethylsilyl)-ethoxy]methyl}-1,4,5,6-tetrahydro-7H-pyrazolo[3,4-b]pyridin-7-yl)phenyl]ethyl}-N,N-dimethyl-1H-imidazole-1-sulfonamide

Product 1

HCID 178442238HCID 178442238, 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 4-(2,2-dimethylpropyl)-2-{1-hydroxy-1-methyl-2-[4-(1-{[2-(trimethylsilyl)ethoxy]methyl}-1,4,5,6-tetrahydro-7H-pyrazolo[3,4-b]pyridin-7-yl)phenyl]ethyl}-N,N-dimethyl-1H-imidazole-1-sulfonamide (1 eq) in methanol (3 mL). After stirring at 70° C. for 1 h, volatiles were removed in vacuo. The residue was purified by 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: 394.

Workup

  1. customvolatiles were removed in vacuo
  2. customThe residue was purified by 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-3493b03400954c67bf3646d048cbeb1b
Source dataset
uspto-grants-2012_01
Patent number
US08106070B2

Reaction notes

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