Sodium Bicarbonate → HCID 57588505, compound

HRID 1782109Notes

Reaction equation

HRID 1782109 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:7]=[C:8]([N:12]3[C:16]4[CH:17]=[C:18]([C:20]([OH:22])=[O:21])[NH:19][C:15]=4[N:14]=[CH:13]3)[CH:9]=[CH:10][CH:11]=2)=[CH:2]1.[C:23](=O)(O)[O-].[Na+]>CO.S(=O)(=O)(O)O>[S:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:7]=[C:8]([N:12]3[C:16]4[CH:17]=[C:18]([C:20]([O:22][CH3:23])=[O:21])[NH:19][C:15]=4[N:14]=[CH:13]3)[CH:9]=[CH:10][CH:11]=2)=[CH:2]1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 68869502HCID 68869502, compound

Product 1

HCID 57588505HCID 57588505, compoundYield 30.3%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of 1-(3-thien-3-ylphenyl)-1,4-dihydropyrrolo[2,3-d]imidazole-5-carboxylic acid (200 mg, 0.65 mmol, prepared as described in the procedure for example 6) in methanol (10 mL) was added concentrated sulfuric acid (5 drops). The solution was heated at reflux for 36 h then cooled to room temperature, basified with aqueous sodium bicarbonate (40 mL) and extracted with CH2Cl2 (2×40 mL). The combined organic extracts were washed with saturated aqueous sodium chloride, dried over sodium sulfate and concentrated in vacuo. The resulting residue was purified twice by silica gel chromatography eluting with MeOH:CH2Cl2 0%→1%) to yield 63.4 mg (30.3%) of methyl 1-(3-thien-3-ylphenyl)-1,4-dihydropyrrolo[2,3-d]imidazole-5-carboxylate EXAMPLE 10. 1H NMR (400 MHz, CDCl3): δ=10.11 (br s, 1H), 8.08 (s, 1H), 7.76-7.74 (m, 1H), 7.58-7.51 (m, 3H), 7.47-7.42 (m, 3H), 6.99 (d, J=1.6 Hz, 1H), 3.93 (s, 3H). MS (ES+): m/z 324.23 (100) [MH+].

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux for 36 h
  3. extractionextracted with CH2Cl2 (2×40 mL)
  4. washThe combined organic extracts were washed with saturated aqueous sodium chloride
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue was purified twice by silica gel chromatography
  8. washeluting with MeOH

Sources & evidence

ORD record
ord-0b538ffc8bcd4c3f95e5a5c7483d1a82
Source dataset
uspto-grants-2009_03
Patent number
US07498354B2

Reaction notes

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