Triethylamine → 4-({4-((7-chloroquinolin-4-yl)amino)cyclohexyl}amino)-6-methyl-2H-chromen-2-one

HRID 2415625Notes

Reaction equation

HRID 2415625 reaction equation
Cl[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][C:7](=[O:12])[CH:6]=[C:5]2OS(C(F)(F)F)(=O)=O.[CH3:21]CN(CC)CC.[Cl:28][C:29]1[CH:38]=[C:37]2[C:32]([C:33]([NH:39][CH:40]3[CH2:45][CH2:44][CH:43]([NH2:46])[CH2:42][CH2:41]3)=[CH:34][CH:35]=[N:36]2)=[CH:31][CH:30]=1.C(#N)C.ClCCl.CN(C=O)C>C(#N)C>[Cl:28][C:29]1[CH:38]=[C:37]2[C:32]([C:33]([NH:39][CH:40]3[CH2:41][CH2:42][CH:43]([NH:46][C:5]4[C:4]5[C:9](=[CH:10][CH:11]=[C:2]([CH3:21])[CH:3]=5)[O:8][C:7](=[O:12])[CH:6]=4)[CH2:44][CH2:45]3)=[CH:34][CH:35]=[N:36]2)=[CH:31][CH:30]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 18391686N-(7-chloroquinolin-4-yl)cyclohexane-1,4-diamineHCID 20817849HCID 20817849, compoundHCID 86590478acetonitrile dichloromethane DMF

Product 1

HCID 226417014-({4-((7-chloroquinolin-4-yl)amino)cyclohexyl}amino)-6-methyl-2H-chromen-2-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a conical microwave vessel (7.5 mL) equipped with a septum cap and a magnetic stirring bar was added a solution of a trifluoro-methanesulfonic acid 6-chloro-2-oxo-2H-chromen-4-yl ester (0.014 g; 0.043 mmol)) in dry acetonitrile (1 mL) containing Et3N (0.025 mL). Then, a solution of N-(7-chloro-quinolin-4-yl)-cyclohexane-1,4-diamine (0.0178 g; 1.5 eq.) in 1:1:1 mixture of acetonitrile/dichloromethane/DMF (1 mL) was added to the vessel and the resulting suspension was irradiated in Personal Chemistry Smith Synthesizer (150° C. for 180 s; 300 W). The resulting solution was evaporated to dryness. The residue was dissolved in 1.5 mL of a 1:1 mixture of DMSO/MeOH and purified by preparative reverse-phase HPLC. MS (DCI/NH3) m/z 433 [M+H]+.

Workup

  1. customTo a conical microwave vessel (7.5 mL) equipped with a septum
  2. customcap
  3. additionwas added to the vessel
  4. customthe resulting suspension was irradiated in Personal Chemistry Smith Synthesizer (150° C. for 180 s; 300 W)
  5. customThe resulting solution was evaporated to dryness
  6. dissolutionThe residue was dissolved in 1.5 mL of a 1:1 mixture of DMSO/MeOH
  7. custompurified by preparative reverse-phase HPLC

Sources & evidence

ORD record
ord-01162cbe560643d9b72ef8b809948593
Source dataset
uspto-grants-2004_11
Patent number
US06818772B2

Reaction notes

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