Propylphosphonic anhydride → HCID 59715927, compound

HRID 2223726Notes

Reaction equation

HRID 2223726 reaction equation
Cl.[N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([NH:12][C:13](=[O:19])[NH:14][CH2:15][C:16]([OH:18])=O)=[CH:4][CH:3]=1.[CH3:20][C:21]1[CH:22]=[C:23]([CH:31]=[CH:32][CH:33]=1)[CH:24]=[C:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1.[CH2:34](P1(=O)OP(CCC)(=O)OP(CCC)(=O)O1)CC>CN(C=O)C>[CH3:20][C:21]1[CH:22]=[C:23]([CH:31]=[CH:32][CH:33]=1)[CH:24]=[C:25]1[CH2:30][CH2:29][N:28]([C:16](=[O:18])[CH2:15][NH:14][C:13]([NH:12][C:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[N:2]=[C:3]([CH3:34])[CH:4]=2)=[O:19])[CH2:27][CH2:26]1

Participants

5

Reactant 3

HCID 111923Propylphosphonic anhydrideHCID 17956460HCID 17956460, compoundHCID 69220283HCID 69220283, compound

Product 1

HCID 59715927HCID 59715927, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of (3-quinolin-4-yl-ureido)-acetic acid hydrochloride (281.7 mg, 1 mmol), 4-(3-methyl-benzylidene)-piperidine (187.3 mg, 1 mmol), TEA (1 mL, 7 mmol) in DMF (4 mL) and T3P (50% in EtOAc, 1 mL, 1.7 mmol) is stirred for 2 h at room temperature. The DMF is evaporated, the residue dissolved in CH2Cl2 (150 mL) and washed with 1M aqueous NaOH (50 mL) and brine (30 mL). The organic phase is dried (Na2SO4), filtered and evaporated to provide the crude title compound.

Workup

  1. customThe DMF is evaporated
  2. dissolutionthe residue dissolved in CH2Cl2 (150 mL)
  3. washwashed with 1M aqueous NaOH (50 mL) and brine (30 mL)
  4. dry with materialThe organic phase is dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-1d530da53278420f8d2426963d8d390b
Source dataset
uspto-grants-2008_05
Patent number
US07375227B2

Reaction notes

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