Sodium Hydroxide → HCID 59728070, compound

HRID 2043353Notes

Reaction equation

HRID 2043353 reaction equation
CN(C)S([N:6]1[CH:10]=[C:9]([CH2:11][N:12]([CH2:21][CH3:22])[C:13]2[N:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][N:14]=2)[N:8]=[CH:7]1)(=O)=O.[OH-].[Na+]>Cl>[CH2:21]([N:12]([CH2:11][C:9]1[NH:8][CH:7]=[N:6][CH:10]=1)[C:13]1[N:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][N:14]=1)[CH3:22]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66552232HCID 66552232, compound

Product 1

HCID 59728070HCID 59728070, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
100 °C

Procedure

4-{[Ethyl-(4-methoxy-pyrimidin-2-yl)-amino]-methyl}-imidazole-1-sulfonic acid dimethylamide (0.265 g, 0.78 mmol) was dissolved in aqueous hydrochloric acid (4 N, 2 ml) and the mixture was stirred at 100° C. for 2 hours. After cooling concentrated sodium hydroxide solution was added slowly until basic pH. The mixture was extracted three times with ethyl acetate. The combined organic layers were dried over magnesium sulfate and evaporated. The residue was purified by flash chromatography, column: Isolute® Flash-NH2 (Separtis); eluent: heptane/ethyl acetate=1:1) to yield a colorless liquid, (0.10 g, 55%); MS (ISP): 234.3 ((M+H)+.).

Workup

  1. additionwas added slowly until basic pH
  2. extractionThe mixture was extracted three times with ethyl acetate
  3. dry with materialThe combined organic layers were dried over magnesium sulfate
  4. customevaporated
  5. customThe residue was purified by flash chromatography, column
  6. customeluent: heptane/ethyl acetate=1:1) to yield a colorless liquid, (0.10 g, 55%)

Sources & evidence

ORD record
ord-65b8caf2b78b42e8b8bbae179c900c2b
Source dataset
uspto-grants-2013_11
Patent number
US08586617B2

Reaction notes

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