N,N-Dimethyl-1,3-propanediamine → 2-(4-{6-Amino-5-[1-(2,6-dichloro-3-fluoro-phenyl)-ethoxy]-pyridin-3-yl}-pyrazol-1-yl)-N-(3-dimethylamino-propyl)-propionamide

HRID 1627577Notes

Reaction equation

HRID 1627577 reaction equation
P(F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.[NH2:24][C:25]1[N:30]=[CH:29][C:28]([C:31]2[CH:32]=[N:33][N:34]([CH:36]([CH3:40])[C:37]([OH:39])=O)[CH:35]=2)=[CH:27][C:26]=1[O:41][CH:42]([C:44]1[C:49]([Cl:50])=[CH:48][CH:47]=[C:46]([F:51])[C:45]=1[Cl:52])[CH3:43].C(N(CC)CC)C.[CH3:60][N:61]([CH3:66])[CH2:62][CH2:63][CH2:64][NH2:65]>CN(C=O)C>[NH2:24][C:25]1[N:30]=[CH:29][C:28]([C:31]2[CH:32]=[N:33][N:34]([CH:36]([CH3:40])[C:37]([NH:65][CH2:64][CH2:63][CH2:62][N:61]([CH3:66])[CH3:60])=[O:39])[CH:35]=2)=[CH:27][C:26]=1[O:41][CH:42]([C:44]1[C:49]([Cl:50])=[CH:48][CH:47]=[C:46]([F:51])[C:45]=1[Cl:52])[CH3:43]

Participants

6

Reactant 4

HCID 7993N,N-Dimethyl-1,3-propanediamineHCID 8471TriethylamineHCID 58659144HCID 58659144, compoundHCID 86603508HCID 86603508, compound

Product 1

HCID 670844182-(4-{6-Amino-5-[1-(2,6-dichloro-3-fluoro-phenyl)-ethoxy]-pyridin-3-yl}-pyrazol-1-yl)-N-(3-dimethylamino-propyl)-propionamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium phosphorus pentafluoride (HATU) (66 mg, 0.17 mmol) was added to a solution of 2-(4-{6-Amino-5-[1-(2,6-dichloro-3-fluoro-phenyl)-ethoxy]-pyridin-3-yl}-pyrazol-1-yl)-propionic acid (69 mg, 0.16 mmol), triethylamine (0.024 mL, 0.17 mmol) and 3-dimethylamino-propylamine (0.022 mL, 0.17 mmol) in 1.6 mL of DMF. After stirring for 3 hours, the reaction was concentrated by rotary evaporation. The residue was purified by silica gel chromatography using gradient elution of dichloromethane, methanol, ammonium hydroxide to afford 2-(4-{6-Amino-5-[1-(2,6-dichloro-3-fluoro-phenyl)-ethoxy]-pyridin-3-yl}-pyrazol-1-yl)-N-(3-dimethylamino-propyl)-propionamide. (41 mg, 50%).

Workup

  1. concentrationthe reaction was concentrated by rotary evaporation
  2. customThe residue was purified by silica gel chromatography
  3. washelution of dichloromethane, methanol, ammonium hydroxide

Sources & evidence

ORD record
ord-5e26fb08159d41b59d5cf3004e36b7a5
Source dataset
uspto-grants-2014_07
Patent number
US08785632B2

Reaction notes

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