N-Methylaniline → HCID 59715920, compound

HRID 2223730Notes

Reaction equation

HRID 2223730 reaction equation
Cl.Cl.[CH3:3][C:4]1[CH:13]=[C:12]([NH:14][C:15](=[O:28])[NH:16][CH2:17][CH2:18][N:19]2[CH2:24][CH2:23][CH:22]([C:25]([OH:27])=O)[CH2:21][CH2:20]2)[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1.[CH3:29][NH:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)O1)CC>CN(C=O)C>[CH3:29][N:30]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:25]([CH:22]1[CH2:23][CH2:24][N:19]([CH2:18][CH2:17][NH:16][C:15]([NH:14][C:12]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]=[C:4]([CH3:3])[CH:13]=2)=[O:28])[CH2:20][CH2:21]1)=[O:27]

Participants

5

Reactant 3

HCID 7515N-MethylanilineHCID 111923Propylphosphonic anhydrideHCID 69217452HCID 69217452, compound

Product 1

HCID 59715920HCID 59715920, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 1-{2-[3-(2-methyl-quinolin-4-yl)-ureido]-ethyl}-piperidine-4-carboxylic acid dihydrochloride (64.25 mg, 0.15 mmol), TEA (0.07 mL, 0.5 mmol) and N-methylaniline (11 mg, 0.1 mmol) in DMF (0.6 mL) is is added T3P (50% in EtOAc, 0.07 mL, 0.12 mmol) at room temperature. The mixture is stirred for 15 h, quenched with sat. Na2CO3 (5 mL) and extracted with CH2Cl2 (3×10 mL). The organic phases are dried (Na2SO4), filtered, evaporated and the residue purified by preparative HPLC to provide the title compound.

Workup

  1. customquenched with sat. Na2CO3 (5 mL)
  2. extractionextracted with CH2Cl2 (3×10 mL)
  3. dry with materialThe organic phases are dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customthe residue purified by preparative HPLC

Sources & evidence

ORD record
ord-f7aaa1c9a6774b04b1e263888db2cfb6
Source dataset
uspto-grants-2008_05
Patent number
US07375227B2

Reaction notes

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