Cesium carbonate → HCID 46205005, compound

HRID 532812Notes

Reaction equation

HRID 532812 reaction equation
Cl[CH2:2][C:3]1[N:4]=[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[S:6][CH:7]=1.Cl.[CH3:15][O:16][C:17]1[CH:22]=[C:21]([O:23][CH3:24])[CH:20]=[CH:19][C:18]=1[N:25]1[CH2:31][CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.CCOC(C)=O>[CH3:15][O:16][C:17]1[CH:22]=[C:21]([O:23][CH3:24])[CH:20]=[CH:19][C:18]=1[N:25]1[CH2:31][CH2:30][CH2:29][N:28]([CH2:2][C:3]2[N:4]=[C:5]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[S:6][CH:7]=2)[CH2:27][CH2:26]1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 2369694-(Chloromethyl)-2-phenyl-1,3-thiazoleHCID 66893177HCID 66893177, compound

Product 1

HCID 46205005HCID 46205005, compoundYield 32.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-chloromethyl-2-phenylthiazole (80 mg, 0.38 mmol, 1 equiv), 1-(2,4-dimethoxyphenyl)-[1,4]diazepane HCl salt (117 mg, 0.38 mmol, 1 equiv) and Cs2CO3 (619 mg, 5 equiv) in 1 mL of DMF was stirred at room temperature overnight. The mixture was diluted with EtOAc (˜30 mL), washed with saturated aqueous NaHCO3 (20 mL) and brine (20 mL) sequentially and then dried over magnesium sulfate. The residue was purified by flash column chromatograph using 30 to 100% EtOAc in hexane to afford the title compound as light tan solid (50 mg) after evaporation and drying in vacuo. 1H NMR (400 MHz, CDCl3) δ 7.90 (d, 2H, J=8.0 Hz), 7.39 (m, 3H), 7.15 (s, 1H), 6.88 (d, 1H, J=8.8 Hz), 6.42 (s, 1H), 6.39 (d, 1H, J=8.8 Hz), 3.91 (s, 2H), 3.79 (s, 3H), 3.74 (s, 3H), 3.25 (m, 4H), 2.92 (m, 4H), 1.98 (m, 2H). MS (ES) m/z 410.2 (M+H+).

Workup

  1. washwashed with saturated aqueous NaHCO3 (20 mL) and brine (20 mL) sequentially
  2. dry with materialdried over magnesium sulfate
  3. customThe residue was purified by flash column chromatograph

Sources & evidence

ORD record
ord-d30285211d784dfcab7adce81a6a773d
Source dataset
uspto-grants-2014_10
Patent number
US08853202B2

Reaction notes

Loading…