Formic Acid → HCID 86712107, compound

HRID 715940Notes

Reaction equation

HRID 715940 reaction equation
[CH2:1]([N:3]([CH2:34][CH3:35])[CH2:4]/[CH:5]=[CH:6]\[C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:8]=1[S:14]([NH:17][C:18]1[C:29]([C:30]([O:32]C)=[O:31])=[C:22]2[N:23]=[C:24]3[CH2:28][CH2:27][CH2:26][N:25]3[C:21]2=[CH:20][CH:19]=1)(=[O:16])=[O:15])[CH3:2].O.[OH-].[Li+].C(O)=O>O1CCOCC1.O.CO>[CH2:34]([N:3]([CH2:1][CH3:2])[CH2:4]/[CH:5]=[CH:6]\[C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:8]=1[S:14]([NH:17][C:18]1[C:29]([C:30]([OH:32])=[O:31])=[C:22]2[N:23]=[C:24]3[CH2:28][CH2:27][CH2:26][N:25]3[C:21]2=[CH:20][CH:19]=1)(=[O:15])=[O:16])[CH3:35]

Participants

7

Reactant 3

HCID 284Formic AcidHCID 168937Lithium hydroxide, monohydrateHCID 86712108HCID 86712108, compound2×

Product 1

HCID 86712107HCID 86712107, compoundYield 22.5%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of methyl 6-[2-((Z)-3-diethylaminoprop-1-enyl)-4-fluorobenzenesulfonylamino]-2,3-dihydro-1H-benzo[d]pyrrolo[1,2-a]imidazole-5-carboxylate (Intermediate 53, 0.16 g) and lithium hydroxide monohydrate (0.526 g) in dioxane (10 mL) and water (2.5 mL) was irradiated in the microwave at 135° C. for 45 minutes. After cooling, the mixture was diluted with methanol, acidified with formic acid and evaporated in vacuo. The residue was azeiotroped with a mixture of toluene and ethanol and the residue was triturated with 20% methanol in DCM and filtered. The filtrate was evaporated in vacuo and the residue was purified by chromatography on silica, eluting with DMAW-60. The resultant solid was further purified by HPLC (C18) to give 6-[2-((Z)-3-diethylaminoprop-1-enyl)-4-fluorobenzenesulfonylamino]-2,3-dihydro-1H-benzo[d]pyrrolo[1,2-a]imidazole-5-carboxylic acid (0.035 g).

Workup

  1. customwas irradiated in the microwave at 135° C. for 45 minutes
  2. temperatureAfter cooling
  3. customevaporated in vacuo
  4. additionThe residue was azeiotroped with a mixture of toluene and ethanol
  5. customthe residue was triturated with 20% methanol in DCM
  6. filtrationfiltered
  7. customThe filtrate was evaporated in vacuo
  8. customthe residue was purified by chromatography on silica
  9. washeluting with DMAW-60
  10. customThe resultant solid was further purified by HPLC (C18)

Sources & evidence

ORD record
ord-d468aa42df5d48df80f76b6d1acad011
Source dataset
uspto-grants-2015_11
Patent number
US09187494B2

Reaction notes

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