Triethylamine → HCID 67951154, compound

HRID 923653Notes

Reaction equation

HRID 923653 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]2[S:9][NH:10][C:11](=[O:12])[C:3]=12.Cl[CH2:14][C:15]([N:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1)=[O:16].CCN(CC)CC>C(Cl)Cl>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]2[S:9][N:10]=[C:11]([O:12][CH2:14][C:15]([N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)=[O:16])[C:3]=12

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 74040Morpholine, 4-(chloroacetyl)-HCID 173760Isothiazolo(5,4-b)pyridin-3(2H)-one, 4,6-dimethyl-

Product 1

HCID 67951154HCID 67951154, compoundYield 9.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

Pyridinothiazolone 4 (200 mg, 1.22 mmol), was treated with 2-chloro-1-morpholinoethanone (225 mg, 1.25 mmol) and Et3N (370 mg, 3.66 mmol) in anhydrous CH2Cl2 (25 mL) at reflux (40° C.) for 24 h, and then washed with 1 M HCl(aq). The organic phase was dried over MgSO4, filtered, concentrated, and purified by flash chromatography on a silica gel column with elution of EtOAc/hexane (1:1) to give the title compound (35 mg, 9% yield) in addition to the main N-alkylation product 19 (55%).

Workup

  1. washwashed with 1 M HCl(aq)
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by flash chromatography on a silica gel column with elution of EtOAc/hexane (1:1)

Sources & evidence

ORD record
ord-cc79e810608d4c4c9b976b1139d63eac
Source dataset
uspto-grants-2016_03
Patent number
US09278982B2

Reaction notes

Loading…