Thionyl Chloride → HCID 67246988, compound

HRID 1190923Notes

Reaction equation

HRID 1190923 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]([CH2:20]O)[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][NH:36][CH3:37]>CN1C(=O)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[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)=[C:18]([CH2:20][N:36]([CH2:35][CH2:34][N:33]([CH3:38])[CH3:32])[CH3:37])[CH:19]=3)=[CH:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 24386Thionyl ChlorideHCID 673381,2-Ethanediamine, N1,N1,N2-trimethyl-HCID 67247174HCID 67247174, compound2×

Product 1

HCID 67246988HCID 67246988, compoundYield 85.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 13387N-methyl-2-pyrrolidoneSolvent2×

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 (1 mL, 7.50 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/NH4OH//90/10/1 then 80/20/1) to yield expected compound as a yellow solid (97 mg, 85% yield). LC-MS: m/z (ESI) 454.4 [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/NH4OH//90/10/1

Sources & evidence

ORD record
ord-470256b229ba43bcb434e9c0cae36e8e
Source dataset
uspto-grants-2014_03
Patent number
US08680095B2

Reaction notes

Loading…