Triphenylphosphine → HCID 57659772, compound

HRID 1011620Notes

Reaction equation

HRID 1011620 reaction equation
N(C(OC(C)C)=O)=NC(OC(C)C)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[F:34][C:35]1[CH:40]=[CH:39][C:38]([CH:41](O)[C:42]2[C:46]([CH2:47][NH:48][S:49]([C:52]3[CH:57]=[CH:56][C:55]([C:58]([F:61])([F:60])[F:59])=[CH:54][CH:53]=3)(=[O:51])=[O:50])=[CH:45][N:44]([CH2:62][O:63][CH3:64])[N:43]=2)=[CH:37][CH:36]=1>C1COCC1>[F:34][C:35]1[CH:40]=[CH:39][C:38]([CH:41]2[C:42]3=[N:43][N:44]([CH2:62][O:63][CH3:64])[CH:45]=[C:46]3[CH2:47][N:48]2[S:49]([C:52]2[CH:57]=[CH:56][C:55]([C:58]([F:61])([F:60])[F:59])=[CH:54][CH:53]=2)(=[O:51])=[O:50])=[CH:37][CH:36]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 57659786HCID 57659786, compound

Product 1

HCID 57659772HCID 57659772, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diisopropyl azodicarboxylate (45 μL, 0.228 mmol) was added dropwise to a stirred solution of triphenylphosphine (60 mg, 0.228 mmol) and N-((3-((4-fluorophenyl)(hydroxy)methyl)-1-(methoxymethyl)-1H-pyrazol-4-yl)methyl)-4-(trifluoromethyl)benzenesulfonamide (45) (90 mg, 0.190 mmol) in THF (5 mL) under nitrogen at 0° C. Reaction was warmed to rt and stirred 16 hr. The reaction was concentrated in vacuo. The resulting crude product was purified via column chromatography using EtOAc/hexane gradients to yield 6-(4-fluorophenyl)-2-(methoxymethyl)-5-(4-(trifluoromethyl)phenylsulfonyl)-2,4,5,6-tetrahydropyrrolo[3,4-c]pyrazole (46) (64 mg, 71%) as a white solid.

Workup

  1. customReaction
  2. concentrationThe reaction was concentrated in vacuo
  3. customThe resulting crude product was purified via column chromatography

Sources & evidence

ORD record
ord-32c381a5e85148f39376117e649037a2
Source dataset
uspto-grants-2011_07
Patent number
US07977368B2

Reaction notes

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