Pyrrolidine → HCID 178518159, compound

HRID 1620664Notes

Reaction equation

HRID 1620664 reaction equation
Cl.[F:2][C:3]([F:34])([F:33])[C:4]1[CH:28]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:26]=[CH:25][C:5]=1[CH2:6][N:7]1[CH2:12][CH2:11][CH:10](/[CH:13]=[C:14]2/[C:15]([NH:20][CH2:21][C:22](O)=[O:23])=[N:16][C:17](=[O:19])[S:18]/2)[CH2:9][CH2:8]1.C([N:37]([CH:41]([CH3:43])C)[CH:38]([CH3:40])C)C.N1CCCC1.F[P-](F)(F)(F)(F)F.C(C(=NO[C+](N(C)C)N1CCOCC1)C(OCC)=O)#N>CN(C=O)C.O>[F:2][C:3]([F:34])([F:33])[C:4]1[CH:28]=[C:27]([C:29]([F:30])([F:32])[F:31])[CH:26]=[CH:25][C:5]=1[CH2:6][N:7]1[CH2:12][CH2:11][CH:10](/[CH:13]=[C:14]2/[C:15]([NH:20][CH2:21][C:22](=[O:23])[N:37]3[CH2:38][CH2:40][CH2:43][CH2:41]3)=[N:16][C:17](=[O:19])[S:18]/2)[CH2:9][CH2:8]1

Participants

7

Reactant 4

HCID 31268PyrrolidineHCID 81531DiisopropylethylamineHCID 178472143HCID 178472143, compoundHCID 178479765HCID 178479765, compound

Product 1

HCID 178518159HCID 178518159, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of N-[(5Z)-5-({1-[2,4-bis(trifluoromethyl)benzyl]piperidin-4-yl}methylidene)-2-oxo-2,5-dihydro-1,3-thiazol-4-yl]glycine hydrochloride (500 mg), N-ethyl-N-(1-methylethyl)propan-2-amine (0.49 mL) and pyrrolidine (0.24 mL) in DMF (5 mL) was added (1-cyano-2-ethoxy-2-oxoethylideneaminooxy)dimethylamino-morpholino-carbenium hexafluorophosphate (403 mg), and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, methanol/ethyl acetate), and the solid was recrystallized from ethyl acetate/heptane to give the title compound (90 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (NH, methanol/ethyl acetate)
  6. customthe solid was recrystallized from ethyl acetate/heptane

Sources & evidence

ORD record
ord-7984c0e63df74a74a8042dd61405f0f5
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

Loading…