4-Fluorobenzoyl chloride → HCID 11859042, compound

HRID 2217351Notes

Reaction equation

HRID 2217351 reaction equation
[NH2:1][C:2]1[C:3]2[CH2:14][N:13]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:12]([CH3:23])([CH3:22])[C:4]=2[N:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:6]=1.C(N(CC)C(C)C)(C)C.[F:33][C:34]1[CH:42]=[CH:41][C:37]([C:38](Cl)=[O:39])=[CH:36][CH:35]=1>C1COCC1>[F:33][C:34]1[CH:42]=[CH:41][C:37]([C:38]([NH:1][C:2]2[C:3]3[CH2:14][N:13]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:12]([CH3:22])([CH3:23])[C:4]=3[N:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:6]=2)=[O:39])=[CH:36][CH:35]=1

Participants

5

Reactant 3

HCID 678794-Fluorobenzoyl chlorideHCID 81531DiisopropylethylamineHCID 573530855-tert-Butyl 1-ethyl 3-amino-6,6-dimethyl-4,6-dihydropyrrolo[3,4-c]pyrazole-1,5-dicarboxylate

Product 1

HCID 11859042HCID 11859042, compoundYield 90.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

5-tert-Butyl 1-ethyl 3-amino-6,6-dimethyl-4,6-dihydropyrrolo[3,4-c]pyrazole-1,5-dicarboxylate (2.0 g, 6.16 mmol) was dissolved in THF (40 ml), treated first with N,N-diisopropylethylamine (5.4 ml, 30.80 mmol) and then, at 0° C., with 4-fluorobenzoyl chloride (800 μl, 6.77 mmol) dissolved in THF (8 ml) dropwise. The reaction mixture was stirred at room temperature for 5 hours, concentrated and dissolved in DCM, washed with saturated sodium hydrogencarbonate aqueous solution and with brine. The organic phase was dried over sodium sulfate, evaporated and purified by flash chromatography (eluent hexane/EtOAc 80/20) to afford 2.5 g of the title compound in 90% yield.

Workup

  1. concentrationconcentrated
  2. dissolutiondissolved in DCM
  3. washwashed with saturated sodium hydrogencarbonate aqueous solution and with brine
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. customevaporated
  6. custompurified by flash chromatography (eluent hexane/EtOAc 80/20)

Sources & evidence

ORD record
ord-14885ebbbef24e3a8876cb084d66fe6a
Source dataset
uspto-grants-2008_08
Patent number
US07407971B2

Reaction notes

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