Dimethylformamide → HCID 23153052, compound

HRID 492708Notes

Reaction equation

HRID 492708 reaction equation
[NH2:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]([NH2:13])[CH:8]=2)=[CH:4][C:3]=1[CH3:16].C(N(CC)CC)C.[F:24][P-](F)(F)(F)(F)F.[N:31]1(O[P+](N(C)C)(N(C)C)N(C)C)[C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=2N=N1.C([O:54][CH2:55][CH3:56])(=O)C.CN(C)[CH:59]=[O:60]>C(OCC)C.C(O)C.C(OCC)(=O)C.CO>[NH2:13][C:9]1[CH:8]=[C:7]([O:6][C:5]2[CH:14]=[CH:15][C:2]([NH:1][C:55](=[O:54])[CH2:56][C:59]([NH:31][C:35]3[CH:36]=[CH:37][C:38]([F:24])=[CH:39][CH:34]=3)=[O:60])=[C:3]([CH3:16])[CH:4]=2)[CH:12]=[CH:11][N:10]=1

Participants

9

Reactant 5

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 23153189HCID 23153189, compound

Product 1

HCID 23153052HCID 23153052, compoundYield 57.5%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 3283Diethyl EtherSolventHCID 21584119Ethylacetate methanolSolvent

Procedure

To a solution of 4-(4-amino-3-methylphenoxy)pyridin-2-ylamine (765 mg, 3.55 mmol) in N,N-dimethylformamide (15.0 ml) were added N-(4-fluorophenyl)malonic acid (770 mg, 3.91 mmol), triethylamine (0.544 ml, 3.91 mmol) and benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (1.73 g, 3.91 mmol), followed by stirring at room temperature for 13 hrs. The reaction mixture was partitioned between ethyl acetate (200 ml) and a saturated aqueous solution of sodium hydrogencarbonate (80 ml). The organic layer was washed with water and brine, and dried over anhydrous sodium sulfate. The solvent was evaporated to give a residue, which was then subjected to silica gel column chromatography (ethyl acetate, then ethyl acetate/methanol=20/1 to 10/1). To the resultant crude product were added ethanol (0.5 ml) and diethyl ether (10 ml) to suspend. A solid was filtered off, washed with diethyl ether, and dried under aeration to provide the titled compound (805 mg, 57.5%) as pale yellow powder.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate (200 ml)
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated
  5. customto give a residue, which
  6. filtrationA solid was filtered off
  7. washwashed with diethyl ether
  8. customdried under aeration

Sources & evidence

ORD record
ord-b1a71939d29248e2b059aa9178e5594d
Source dataset
uspto-grants-2009_05
Patent number
US07531532B2

Reaction notes

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