Triethylamine → HCID 67951153, compound

HRID 923658Notes

Reaction equation

HRID 923658 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.I[CH2:14][C:15]([N:17]1[CH2:22][CH2:21][N:20]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:19][CH2:18]1)=[O:16].CCN(CC)CC.C([O-])([O-])=O.[Cs+].[Cs+]>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][N:20]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:19][CH2:18]3)=[O:16])[C:3]=12

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10796Cesium carbonateHCID 173760Isothiazolo(5,4-b)pyridin-3(2H)-one, 4,6-dimethyl-HCID 67811489HCID 67811489, compound

Product 1

HCID 67951153HCID 67951153, compoundYield 11%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Pyridinothiazolone 4 (300 mg, 1.66 mmol) was treated with ethyl 4-(2-iodoacetyl)piperazine-1-carboxylate (541 mg, 1.66 mmol), Et3N (840 mg, 8.30 mmol) and Cs2CO3 (500 mg, 1.54 mmol) in anhydrous CH2Cl2 (25 mL) at room temperature for 24 h, and then washed with H2O. The organic layer was dried over MgSO4, filtered, concentrated, and purified by flash chromatography on a silica gel column (EtOAc/hexane (1:1)) to give the title compound (68 mg, 11% yield) in addition to the main N-alkylation product 21 (YMU1, 60%). The purity of product 28 was 99.5% as shown by HPLC on an HC-C18 column (Agilent, 4.6×250 mm, 5 μM), t R=4.9 min (gradients of 40-90% aqueous CH3CN in 15 min).

Workup

  1. washwashed with H2O
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by flash chromatography on a silica gel column (EtOAc/hexane (1:1))

Sources & evidence

ORD record
ord-633dba71f1ad4306a1bb28188a6b4e8d
Source dataset
uspto-grants-2016_03
Patent number
US09278982B2

Reaction notes

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