Water → HCID 57691377, compound

HRID 219104Notes

Reaction equation

HRID 219104 reaction equation
[CH3:1][N:2]([CH3:12])[C:3]1[N:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.Cl[C:14]1[CH:15]=[CH:16][C:17]2[N:18]([C:20]([CH2:23][O:24][C:25]3[C:34]4[C:29](=[CH:30][C:31]([O:35][CH3:36])=[CH:32][CH:33]=4)[N:28]=[CH:27][CH:26]=3)=[N:21][N:22]=2)[N:19]=1.CN(C=O)C.C(=O)([O-])[O-].[K+].[K+].O>>[CH3:36][O:35][C:31]1[CH:30]=[C:29]2[C:34]([C:25]([O:24][CH2:23][C:20]3[N:18]4[N:19]=[C:14]([C:6]5[CH:5]=[CH:4][C:3]([N:2]([CH3:12])[CH3:1])=[N:8][CH:7]=5)[CH:15]=[CH:16][C:17]4=[N:22][N:21]=3)=[CH:26][CH:27]=[N:28]2)=[CH:33][CH:32]=1

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 27632716-(Dimethylamino)pyridine-3-boronic acidHCID 250669924-((6-Chloro-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methoxy)-7-methoxyquinoline

Product 1

HCID 57691377HCID 57691377, compound

Conditions

Temperature
80 °C

Procedure

A 48 mL tube was charged with 6-(dimethylamino)pyridin-3-ylboronic acid (0.109 g, 0.658 mmol), 4-((6-chloro-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methoxy)-7-methoxyquinoline (0.150 g, 0.439 mmol), and DMF (3.00 ml, 38.6 mmol), and stirred for 10 minutes. A solution of potassium carbonate (0.182 g, 1.32 mmol) and water (0.696 ml, 38.6 mmol) was added, followed by PdCl2(dppf)-CH2Cl2Adduct (0.0358 g, 0.0439 mmol). The tube was flushed with argon, sealed, and heated in a 80° C. oil bath for 5 hours. The mixture was concentrated, and the residue was triturated with water to give a brown solid which was purified by MPLC using a 40 g column, eluting with 1-5% MeOH/DCM over 40 minutes to give 5-(3-((7-methoxyquinolin-4-yloxy)methyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)-N,N-dimethylpyridin-2-amine as a dark green solid. MS (ESI pos. ion) m/z: 428 (MH+). Calc'd exact mass for C23H18FN5O2: 427.

Workup

  1. customThe tube was flushed with argon
  2. customsealed
  3. concentrationThe mixture was concentrated
  4. customthe residue was triturated with water
  5. customto give a brown solid which
  6. customwas purified by MPLC
  7. washeluting with 1-5% MeOH/DCM over 40 minutes

Sources & evidence

ORD record
ord-cb8955b1e09f42b0b9127e0cceed5e21
Source dataset
uspto-grants-2012_06
Patent number
US08198448B2

Reaction notes

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