Hydrochloric Acid → HCID 57588501, compound

HRID 1782103Notes

Reaction equation

HRID 1782103 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]3[CH:13]=[C:14]([C:16]([O:18]CC)=[O:17])[NH:15][C:11]=3[N:10]=[CH:9]2)=[CH:4][CH:3]=1.[OH-].[Na+].Cl>C(O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]3[CH:13]=[C:14]([C:16]([OH:18])=[O:17])[NH:15][C:11]=3[N:10]=[CH:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 11842687HCID 11842687, compound

Product 1

HCID 57588501HCID 57588501, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of ethyl 1-(4-bromophenyl)-1,4-dihydropyrrolo[2,3-d]imidazole-5-carboxylate (EXAMPLE 1) (95 mg) in ethanol (3 mL) was added 1 mL of 3N NaOH and the mixture heated at reflux for 6 h, after which time mixture was cooled to rt and acidified with 3N HCl to pH=3. The resulting off-white solid was collected by filtration to yield 1-(4-bromophenyl)-1,4-dihydropyrrolo[2,3-d]imidazole-5-carboxylic acid. LC-MS (ES+): m/z 306/308 (1/1) [MH+]. 1H NMR (DMSO-d6, 400 MHz): δ=7.18 (d, J=1.0 Hz, 1H), 7.86 (d, J=9.0 Hz, 2H), 7.92 (d, J=9.0 Hz, 2H), 8.69 (s, 1H), 12.15 (s, 1H, NH).

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 6 h
  3. filtrationThe resulting off-white solid was collected by filtration

Sources & evidence

ORD record
ord-74121647bdbe46a59ddd8d49912b0259
Source dataset
uspto-grants-2009_03
Patent number
US07498354B2

Reaction notes

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