Bis(2-chloroethyl) ether → HCID 178422096, compound

HRID 2360300Notes

Reaction equation

HRID 2360300 reaction equation
[NH2:1][CH2:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]([CH:32]=[CH:33][CH:34]=1)[C:8]([N:10]1[CH2:15][CH2:14][CH:13]([CH2:16][C:17]2([CH3:31])[S:21][C:20]([NH:22][C@H:23]3[CH2:28][CH:27]4[CH2:29][CH:24]3[CH2:25][CH2:26]4)=[N:19][C:18]2=[O:30])[CH2:12][CH2:11]1)=[O:9].C([O-])([O-])=O.[K+].[K+].Cl[CH2:42][CH2:43][O:44][CH2:45][CH2:46]Cl.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH:24]12[CH2:29][CH:27]([CH2:26][CH2:25]1)[CH2:28][C@@H:23]2[NH:22][C:20]1[S:21][C:17]([CH3:31])([CH2:16][CH:13]2[CH2:14][CH2:15][N:10]([C:8](=[O:9])[C:7]3[CH:32]=[CH:33][CH:34]=[C:5]([O:4][CH2:3][CH2:2][N:1]4[CH2:46][CH2:45][O:44][CH2:43][CH2:42]4)[CH:6]=3)[CH2:11][CH2:12]2)[C:18](=[O:30])[N:19]=1

Participants

6

Reactant 4

HCID 8115Bis(2-chloroethyl) etherHCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 178422098HCID 178422098, compound

Product 1

HCID 178422096HCID 178422096, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 5-((1-(3-(2-aminoethoxy)benzoyl)piperidin-4-yl)methyl)-2-((2S)-bicyclo[2.2.1]heptan-2-ylamino)-5-methylthiazol-4(5H)-one (100 mg, 0.207 mmol), K2CO3 (114 mg, 0.83 mmol), KI (Aldrich, 6.9 mg, 0.041 mmol), 1-chloro-2-(2-chloroethoxy)ethane (Aldrich, 38 mg, 0.27 mmol) in CH2Cl2 (3 mL) was heated at reflux for 10 d. Saturated NaHCO3 (50 mL) was added, and the crude product was extracted with CH2Cl2 (4×60 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. Flash column chromatography (silica gel, CH2Cl2 with 0-4% MeOH) afforded the title compound as a colorless thin film (10 mg). MS (ESI, pos. ion) m/z: 555 (M+H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 10 d
  3. extractionthe crude product was extracted with CH2Cl2 (4×60 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1619d8632d844e6abe46a7bdc420b31d
Source dataset
uspto-grants-2014_04
Patent number
US08686011B2

Reaction notes

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