Sodium Hydroxide → HCID 178463763, compound

HRID 2043357Notes

Reaction equation

HRID 2043357 reaction equation
CN(C)S([N:6]1[CH:10]=[C:9]([CH2:11][N:12]([CH2:26][CH3:27])[C:13]2[CH:18]=[CH:17][N:16]=[C:15]([O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[N:14]=2)[N:8]=[CH:7]1)(=O)=O.[OH-].[Na+]>Cl.C(O)C>[CH2:26]([N:12]([CH2:11][C:9]1[N:8]=[CH:7][NH:6][CH:10]=1)[C:13]1[CH:18]=[CH:17][N:16]=[C:15]([O:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:14]=1)[CH3:27]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 66751337HCID 66751337, compound

Product 1

HCID 178463763HCID 178463763, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

To remove the dimethylaminosulfonyl protecting group 4-{[ethyl-(2-phenoxy-pyrimidin-4-yl)-amino]-methyl}-imidazole-1-sulfonic acid dimethylamide (65 mg, 0.16 mmol) was dissolved in hydrochloric acid in ethanol (5 N, 1 ml) and the mixture was stirred at 100° C. for 2 hours. For workup aqueous sodium hydroxide solution (0.5 ml, 1 N) was added to basic pH and the mixture was extracted three times with dichloromethane. The combined organic layers were dried over magnesium sulfate and evaporated. The residue was purified by flash chromatography (SiO2; ethyl acetate/methanol=95:5) to yield a white solid, (0.022 g, 46%); MS (ISP): 296.3 ((M+H)+.).

Workup

  1. extractionthe mixture was extracted three times with dichloromethane
  2. dry with materialThe combined organic layers were dried over magnesium sulfate
  3. customevaporated
  4. customThe residue was purified by flash chromatography (SiO2; ethyl acetate/methanol=95:5)
  5. customto yield a white solid, (0.022 g, 46%)

Sources & evidence

ORD record
ord-4a4c843c01e64a2fad1fdff7dd598241
Source dataset
uspto-grants-2013_11
Patent number
US08586617B2

Reaction notes

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