Triethylamine → 5-Bromo-3-(4-(4-methylpiperazin-1-yl)phenylamino)picolinonitrile

HRID 535903Notes

Reaction equation

HRID 535903 reaction equation
[Br:1][C:2]1[CH:3]=[C:4](F)[C:5]([C:8]#[N:9])=[N:6][CH:7]=1.[CH3:11][N:12]1[CH2:17][CH2:16][N:15]([C:18]2[CH:24]=[CH:23][C:21]([NH2:22])=[CH:20][CH:19]=2)[CH2:14][CH2:13]1.C(N(CC)CC)C>C(O)(C)C>[Br:1][C:2]1[CH:3]=[C:4]([NH:22][C:21]2[CH:20]=[CH:19][C:18]([N:15]3[CH2:14][CH2:13][N:12]([CH3:11])[CH2:17][CH2:16]3)=[CH:24][CH:23]=2)[C:5]([C:8]#[N:9])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 7372534-(4-Methylpiperazin-1-yl)anilineHCID 441966805-Bromo-3-fluoropyridine-2-carbonitrile

Product 1

HCID 704984275-Bromo-3-(4-(4-methylpiperazin-1-yl)phenylamino)picolinonitrile

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 5-bromo-3-fluoropicolinonitrile (1 g, 5 mmol), from EXAMPLE 49A, and 4-(4-methylpiperazin-1-yl)aniline (1.24 g, 6.5 mmol) in isopropanol (15 mL) was treated with triethylamine (0.76 mL, 7.5 mmol) was subjected to microwave irradiation (Biotage, Initiator) at 180° C. for 2 hours. The reaction mixture was concentrated and purified on silica gel with 2-25% methanol in dichloromethane to afford the title compound.

Workup

  1. customwas subjected to microwave irradiation (Biotage, Initiator) at 180° C. for 2 hours
  2. concentrationThe reaction mixture was concentrated
  3. custompurified on silica gel with 2-25% methanol in dichloromethane

Sources & evidence

ORD record
ord-df63f681c736471b955f6d432f0e4ef0
Source dataset
uspto-grants-2014_10
Patent number
US08859546B2

Reaction notes

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