Dimethyl Sulfoxide → HCID 59427282, compound

HRID 1013681Notes

Reaction equation

HRID 1013681 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]#[N:13])=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.[CH2:14]([C:16]1[CH:21]=[C:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:19]=[N:18][C:17]=1[NH:28][C:29]1[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][CH:30]=1)[CH3:15].C(=O)([O-])[O-:37].[Cs+].[Cs+].CS(C)=O>O>[CH2:14]([C:16]1[CH:21]=[C:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:19]=[N:18][C:17]=1[NH:28][C:29]1[CH:30]=[CH:31][C:32]([O:35][C:2]2[C:11]3[C:6](=[CH:7][C:8]([C:12]([NH2:13])=[O:37])=[CH:9][CH:10]=3)[N:5]=[CH:4][CH:3]=2)=[CH:33][CH:34]=1)[CH3:15]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 10796Cesium carbonateHCID 220545814-Chloroquinoline-7-carbonitrileHCID 136131615HCID 136131615, compound

Product 1

HCID 59427282HCID 59427282, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A microwave reaction vial was charged with 4-chloroquinoline-7-carbonitrile (97.1 mg, 0.515 mmol), 4-(4-ethyl-6-phenylpyridazin-3-ylamino)phenol (150 mg, 0.515 mmol), cesium carbonate (252 mg, 0.772 mmol) and 2.6 mL of DMSO. The vial was sealed, and the reaction mixture was irradiated in the microwave at 150° C. for 15 min. Upon cooling the mixture was poured into water and the resulting solids were filtered and washed with water. The crude solids were dissolved in 90/10/1 CH2Cl2/MeOH/NH4OH and purified by silica gel chromatography, 5-100% 90/10/1: CH2Cl2 over 25 min which provided 4-(4-(4-ethyl-6-phenylpyridazin-3-ylamino)phenoxy)quinoline-7-carboxamide as a tan solid. MS m/z=462 [M+H]+. Calc'd for C28H23N3O2: 461.52.

Workup

  1. customA microwave reaction
  2. customThe vial was sealed
  3. customthe reaction mixture was irradiated in the microwave at 150° C. for 15 min
  4. temperatureUpon cooling the mixture
  5. filtrationthe resulting solids were filtered
  6. washwashed with water
  7. dissolutionThe crude solids were dissolved in 90/10/1 CH2Cl2/MeOH/NH4OH
  8. custompurified by silica gel chromatography, 5-100% 90/10/1

Sources & evidence

ORD record
ord-379d9f7e6c1e4726952a706a085cdc24
Source dataset
uspto-grants-2011_07
Patent number
US07981891B2

Reaction notes

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