Cesium carbonate → HCID 67951151, compound

HRID 923651Notes

Reaction equation

HRID 923651 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.Br[CH2:14][C:15]([O:17][CH3:18])=[O:16].C([O-])([O-])=O.[Cs+].[Cs+].CCN(C(C)C)C(C)C>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]([O:17][CH3:18])=[O:16])[C:3]=12

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 60984Methyl bromoacetateHCID 81531DiisopropylethylamineHCID 173760Isothiazolo(5,4-b)pyridin-3(2H)-one, 4,6-dimethyl-

Product 1

HCID 67951151HCID 67951151, compoundYield 7.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of pyridinothiazolone 4 (500 mg, 2.77 mmol), methyl 2-bromoacetate (900 mg, 5.88 mmol), Cs2CO3 (700 mg, 3.07 mmol) and DIEA (1.5 mL, 8.61 mmol) in anhydrous CH2Cl2 (20 mL) was stirred at room temperature for 5 h, and then concentrated under reduced pressure. In addition to the main N-alkylation product 7 (55%), the title compound (50 mg, 7% yield) was obtained after purification by flash chromatography on a silica gel column (EtOAc/hexane (1:4)). C11H12N2O3S; white solid; mp 89-91° C.; IR vmax (neat) 3053, 2958, 2929, 2851, 1767, 1592, 1562, 1504, 1445, 1398, 1334, 1228, 1128, 1039, 961 cm−1; 1H NMR (400 MHz, CDCl3) δ 6.91 (1H, s), 5.05 (2H, s), 3.78 (3H, s), 2.89 (3H, s), 2.61 (3H, s); 13C NMR (100 MHz, CDCl3) δ 172.3, 168.4, 160.7, 160.2, 145.6, 121.4, 115.7, 64.2, 52.3, 24.6, 19.1; ESI-HRMS calcd for C11H13N2O3S: 253.0647. found: m/z 253.0647 [M+H]+.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionIn addition to the main N-alkylation product 7 (55%)

Sources & evidence

ORD record
ord-3b5dffc6d0e14fda8b360032d8e811e1
Source dataset
uspto-grants-2016_03
Patent number
US09278982B2

Reaction notes

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