P-Anisidine → HCID 11555320, compound

HRID 735809Notes

Reaction equation

HRID 735809 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[O:11][C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)[CH:4]=[C:3]1[C:18]([OH:20])=O.CCN([CH:27]([CH3:29])[CH3:28])C(C)C.CN(C(O[N:38]1N=N[C:40]2[CH:41]=[CH:42][CH:43]=[N:44][C:39]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH:54]1C=NC2N(O)N=NC=2C=1.C[O:65][C:66]1[CH:71]=[CH:70][C:69](N)=CC=1.C[CH2:74][O:75][C:76](C)=O>CN(C=O)C>[C:27]([C:41]1[CH:40]=[C:39]([N:38]2[CH2:69][CH2:70][CH2:71][C:66]2=[O:65])[C:74]([O:75][CH3:76])=[C:43]([NH:44][C:18]([C:3]2[N:2]([CH3:1])[C:10]3[C:5]([CH:4]=2)=[CH:6][CH:7]=[CH:8][C:9]=3[O:11][C:12]2[CH:13]=[CH:14][N:15]=[CH:16][CH:17]=2)=[O:20])[CH:42]=1)([CH3:29])([CH3:54])[CH3:28]

Participants

8

Reactant 6

HCID 7732P-AnisidineHCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 22025245HCID 22025245, compound

Product 1

HCID 11555320HCID 11555320, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 1-methyl-7-(pyridine-4-yloxy)-1H-indole-2-carboxylic acid (40 mg, 0.15 mmol) in DMF (1 mL) was added Hunig's base (52 microL, 0.3 mmol) resulting in a clear solution. After 5 min, HATU (90 mg, 0.23 mmol) and HOAT (3 mg, 0.02 mmol) were added followed by the above anisidine (39 mg, 0.15 mmol). The mixture was stirred overnight. The reaction mixture was diluted with EtOAc (30 mL), washed with water, brine, dried over anhydrous Na2SO4 and concentrated in vacuo. The crude product was purified by column chromatography (eluting with 30-80% EtOAc in hexane) to give the title compound (60 mg, 78%).

Workup

  1. customresulting in a clear solution
  2. washwashed with water, brine
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by column chromatography (eluting with 30-80% EtOAc in hexane)

Sources & evidence

ORD record
ord-a57ad4a8c0b54abcb6a8cdf634e36253
Source dataset
uspto-grants-2009_09
Patent number
US07592332B2

Reaction notes

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