3-Fluorophenyl isocyanate → HCID 68654593, compound

HRID 1042381Notes

Reaction equation

HRID 1042381 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.[F:24][C:25]1[CH:26]=[C:27]([N:31]=[C:32]=[O:33])[CH:28]=[CH:29][CH:30]=1>C1COCC1>[F:24][C:25]1[CH:26]=[C:27]([NH:31][C:32]([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:33])[CH:28]=[CH:29][CH:30]=1

Participants

4

Reactant 2

HCID 1230643-Fluorophenyl isocyanateHCID 573530855-tert-Butyl 1-ethyl 3-amino-6,6-dimethyl-4,6-dihydropyrrolo[3,4-c]pyrazole-1,5-dicarboxylate

Product 1

HCID 68654593HCID 68654593, compoundYield 71.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-tert-Butyl 1-ethyl 3-amino-6,6-dimethyl-4,6-dihydropyrrolo[3,4-c]pyrazole-1,5-dicarboxylate (3.0 g, 9.24 mmol) was dissolved in anhydrous THF (50 ml), treated at room temperature with 3-fluorophenyl-isocyanate (1.4 g, 10.21 mmol, 1.1 eq) and stirred overnight. The following day the reaction mixture was evaporated, taken up with DCM and washed with brine. The organic phase was dried over sodium sulfate and evaporated to dryness. Purification by flash chromatography (CH2Cl2/MeOH 90/10) afforded 3.05 g (yield 71%) of the title compound.

Workup

  1. customThe following day the reaction mixture was evaporated
  2. washwashed with brine
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. customevaporated to dryness
  5. customPurification by flash chromatography (CH2Cl2/MeOH 90/10)

Sources & evidence

ORD record
ord-a6e61c346ffe484d8c53c6d892911491
Source dataset
uspto-grants-2013_10
Patent number
US08557845B2

Reaction notes

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