Triethylamine → HCID 18939012, compound

HRID 356692Notes

Reaction equation

HRID 356692 reaction equation
[C:1]1([C:7]2[NH:8][C:9]([C:18]3[CH:23]=[CH:22][C:21]([C:24]([OH:26])=O)=[CH:20][CH:19]=3)=[CH:10][C:11]=2[C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.[F:47][P-](F)(F)(F)(F)F.[NH2:54][CH2:55][C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][N:57]=1.C(N(CC)CC)C>CN(C=O)C>[F:47][C:4]1[CH:5]=[CH:6][C:1]([C:7]2[NH:8][C:9]([C:18]3[CH:23]=[CH:22][C:21]([C:24]([NH:54][CH2:55][C:56]4[CH:61]=[CH:60][CH:59]=[CH:58][N:57]=4)=[O:26])=[CH:20][CH:19]=3)=[CH:10][C:11]=2[C:12]2[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=2)=[CH:2][CH:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 195092-PyridinemethanamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 44323661HCID 44323661, compound

Product 1

HCID 18939012HCID 18939012, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 42 mg (0.124 mmol) 2-phenyl-3-(4-pyridyl)-5-[(4-carboxy)phenyl]-1H-pyrrole (prepared according to Example 51) in 800 uL DMF was added 1.5 equivalents BOP reagent (benzotriazol-1-yloxy-tris-(dimethylamino)phosphonium hexafluorophosphate), 1.2 equivalents 2-(aminomethyl)pyridine, and 2.5 equivalents triethylamine. The mixture was stirred at room temperature for 15 hours. The reaction was quenched by the addition of 5% NaHCO3 solution and ethyl acetate (EtOAc). After separation of phases, the aqueous phase was re-extracted with EtOAc. The combined organic layers were washed with 5% NaHCO3 solution, water, brine, and dried over Na2SO4. After filtration and concentration of the filtrate in vacuo, the crude product was flash chromatographed (gradient elution with 1.0%-5.0% MeOH/CH2Cl2) to the desired product as a cream-colored solid, homogeneous by TLC. FAB ms: Calc.: 430 for C28 H22N4O; Obs.: 431 (M+ +1).

Workup

  1. customThe reaction was quenched by the addition of 5% NaHCO3 solution and ethyl acetate (EtOAc)
  2. customAfter separation of phases
  3. extractionthe aqueous phase was re-extracted with EtOAc
  4. washThe combined organic layers were washed with 5% NaHCO3 solution, water, brine
  5. dry with materialdried over Na2SO4
  6. filtrationAfter filtration and concentration of the filtrate in vacuo
  7. customchromatographed
  8. wash(gradient elution with 1.0%-5.0% MeOH/CH2Cl2) to the desired product as a cream-colored solid

Sources & evidence

ORD record
ord-d052a0d35a1240a5b19233f9ab21638c
Source dataset
uspto-grants-1998_11
Patent number
US05837719

Reaction notes

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