N-methyl-2-pyrrolidone → HCID 53251139, compound

HRID 1190924Notes

Reaction equation

HRID 1190924 reaction equation
Cl.[Cl:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([NH:13][C:14]3[CH:15]=[CH:16][C:17]([N:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)=[C:18](CO)[CH:19]=3)=[CH:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1.S(Cl)(Cl)=O.[CH3:32][N:33]([CH3:38])[CH2:34][CH2:35]NC.CN1[C:44](=[O:45])CCC1>C(Cl)Cl>[Cl:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([NH:13][C:14]3[CH:15]=[CH:16][C:17]([N:22]4[CH2:23][CH2:24][O:25][CH2:26][CH2:27]4)=[C:18]([CH2:32][N:33]4[CH2:38][CH2:44][O:45][CH2:35][CH2:34]4)[CH:19]=3)=[CH:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 13387N-methyl-2-pyrrolidone2×HCID 24386Thionyl ChlorideHCID 673381,2-Ethanediamine, N1,N1,N2-trimethyl-HCID 67247174HCID 67247174, compound2×

Product 1

HCID 53251139HCID 53251139, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of {5-[(7-chloroquinolin-4-yl)amino]-2-(morpholin-4-yl)phenyl}methanol hydrochloride (compound of step C of example 31) (0.100 g, 0.25 mmol) in 4 mL of NMP at 0° C. was added thionyl chloride (90 μL, 1.23 mmol). The reaction mixture was warmed up to room temperature and stirred for 3 h. The reaction mixture was then slowly added to N,N,N′-trimethylethylenediamine (0.65 mL, 7.38 mmol) in 1 mL of NMP at 0° C. and then stirred at room temperature for 2 h. This solution was diluted in 100 mL of CH2Cl2 and washed with a saturated aqueous solution of NaHCO3. The organic layer was dried over MgSO4, filtered, evaporated and purified by flash chromatography (DCM/MeOH///90/10) to yield expected compound as a yellow solid (83 mg, 77% yield). LC-MS: m/z (ESI) 439.3 [M+H]+.

Workup

  1. stirringstirred at room temperature for 2 h
  2. washwashed with a saturated aqueous solution of NaHCO3
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. custompurified by flash chromatography (DCM/MeOH///90/10

Sources & evidence

ORD record
ord-7f1bcf292e504076af8d33aeed4f4c23
Source dataset
uspto-grants-2014_03
Patent number
US08680095B2

Reaction notes

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