Thionyl Chloride → HCID 53250975, compound

HRID 1190920Notes

Reaction equation

HRID 1190920 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.[NH:32]1[CH2:36][CH2:35][CH2:34][CH2:33]1>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:32]4[CH2:36][CH2:35][CH2:34][CH2:33]4)[CH:19]=3)=[CH:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 24386Thionyl ChlorideHCID 31268PyrrolidineHCID 67247174HCID 67247174, compound

Product 1

HCID 53250975HCID 53250975, compoundYield 96%

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 (0.105 g, 0.26 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 pyrrolidine (0.65 mL, 7.75 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) to yield expected compound as a yellow solid (105 mg, 96% yield). LC-MS: m/z (ESI) 423.3 [M+H]+. mp=187-188° C.

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-fab30f863efe450f939a2c057acbe86d
Source dataset
uspto-grants-2014_03
Patent number
US08680095B2

Reaction notes

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