Hydrochloric Acid → HCID 68869502, compound

HRID 1782107Notes

Reaction equation

HRID 1782107 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]([O:22]CC)=[O:21])[NH:19][C:15]=4[N:14]=[CH:13]3)[CH:9]=[CH:10][CH:11]=2)=[CH:2]1.[OH-].[Na+].Cl>C1COCC1>[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

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68870046HCID 68870046, compound

Product 1

HCID 68869502HCID 68869502, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of ethyl 1-(3-thien-3-ylphenyl)-1,4-dihydropyrrolo[2,3-d]imidazole-5-carboxylate (500 mg, 1.5 mmol, prepared as described in the procedure for example 5) in THF (10 mL) was added aqueous sodium hydroxide (416 mg in 4 mL H2O, 10.4 mmol) and the mixture heated at reflux for 16 hr. After this time, the cooled mixture was acidified with 2M HCl to pH 6 and the resulting precipitate collected by filtration, and washed with water and hexane. The filtrate was concentrated to about half the volume and extracted with ethyl acetate (2×75 mL). The combined organic phases were washed with saturated aqueous sodium chloride, and dried over sodium sulfate and evaporated in vacuo to yield a brown solid. The solids were combined and purified by silica gel chromatography eluting with MeOH:CH2Cl2 10%→25%) to yield 312.7 mg (68%) 1-(3-thien-3-ylphenyl)-1,4-dihydropyrrolo[2,3-d]imidazole-5-carboxylic acid. 1H NMR (400 MHz, DMSO-d6): δ=8.39 (s, 1H), 8.07 (d, 2.4 Hz, 1H), 8.04-8.02 (m, 1H), 7.72-7.69 (m, 3H), 7.69-7.57 (m, 3H), 6.66 (br s, 1H). MS (ES+): m/z 338.13 (100) [MH+].

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 16 hr
  3. filtrationthe resulting precipitate collected by filtration
  4. washwashed with water and hexane
  5. concentrationThe filtrate was concentrated to about half the volume
  6. extractionextracted with ethyl acetate (2×75 mL)
  7. washThe combined organic phases were washed with saturated aqueous sodium chloride
  8. dry with materialdried over sodium sulfate
  9. customevaporated in vacuo
  10. customto yield a brown solid
  11. custompurified by silica gel chromatography
  12. washeluting with MeOH

Sources & evidence

ORD record
ord-28461a2369bb4d2cbe3b1308af601c93
Source dataset
uspto-grants-2009_03
Patent number
US07498354B2

Reaction notes

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