1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 69522703, compound

HRID 348442Notes

Reaction equation

HRID 348442 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[CH:12]=[N:13][C:14](S(C)=O)=[N:15][CH:16]=2)=[O:10])=[CH:4][CH:3]=1.[C:20]([O:30][CH3:31])(=[O:29])[C@@H:21]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[OH:22].C1CCN2C(=NCCC2)CC1>C1COCC1>[CH3:31][O:30][C:20](=[O:29])[C@H:21]([O:22][C:14]1[N:13]=[CH:12][C:11]([C:9](=[O:10])[NH:8][C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[CH:16][N:15]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 2724623(R)-(-)-Methyl mandelateHCID 867603842-Methanesulfinylpyrimidine-5-carboxylic acid (4-fluorophenyl)amide

Product 1

HCID 69522703HCID 69522703, compoundYield 34.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 2-methanesulfinylpyrimidine-5-carboxylic acid (4-fluorophenyl)amide (100 mg, 0.36 mmol) and (R)-(−)-methyl mandelate (86 mg, 0.52 mmol) in 3.6 mL of THF was treated dropwise with DBU (80 μL, 0.54 mmol) at ambient temperature. The reaction mixture clarified and turned yellow over the course of 5 min. The reaction was quenched after 24 hours by the addition of 5 mL of 1 M HCl. The mixture was extracted with 2×25 mL portions of ethyl acetate. The organic extracts were combined, dried using Na2SO4 and concentrated in vacuo. The crude material was dissolved in 30% (v/v) ethyl acetate/hexanes and filtered though a 10 g plug of silica gel. The eluent was concentrated to dryness and triturated with 3×5 mL portions of hexane followed by 3×10 mL portions of 10% (v/v) portions of ethyl acetate/hexanes. The residue was dried to yield 47 mg (34%) of the titled compound as a white solid. ESI-MS m/z 382 (MH+), 380 (M−H−).

Workup

  1. customturned yellow over the course of 5 min
  2. customThe reaction was quenched after 24 hours by the addition of 5 mL of 1 M HCl
  3. extractionThe mixture was extracted with 2×25 mL portions of ethyl acetate
  4. customdried
  5. concentrationconcentrated in vacuo
  6. dissolutionThe crude material was dissolved in 30% (v/v) ethyl acetate/hexanes
  7. filtrationfiltered though a 10 g plug of silica gel
  8. concentrationThe eluent was concentrated to dryness
  9. customtriturated with 3×5 mL portions of hexane
  10. customThe residue was dried

Sources & evidence

ORD record
ord-cd581e45f94f4679b2e7e8f5d8e1710b
Source dataset
uspto-grants-2007_02
Patent number
US07176310B1

Reaction notes

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