Potassium Carbonate → (S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(1-oxo-2,7-naphthyridin-2(1H)-yl)benzo[d]thiazol-6-yl)acetate

HRID 879382Notes

Reaction equation

HRID 879382 reaction equation
Br[C:2]1[S:3][C:4]2[C:10]([C:11]3[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=3)=[C:9]([C@H:18]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])[C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:8]([CH3:29])=[CH:7][C:5]=2[N:6]=1.[C:30]1(=[O:40])[C:39]2[C:34](=[CH:35][CH:36]=[N:37][CH:38]=2)[CH:33]=[CH:32][NH:31]1.CN[C@@H]1CCCC[C@H]1NC.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOC(C)=O.[Cu]I>[C:25]([O:24][C@@H:18]([C:9]1[C:8]([CH3:29])=[CH:7][C:5]2[N:6]=[C:2]([N:31]3[CH:32]=[CH:33][C:34]4[C:39](=[CH:38][N:37]=[CH:36][CH:35]=4)[C:30]3=[O:40])[S:3][C:4]=2[C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)[C:19]([O:21][CH2:22][CH3:23])=[O:20])([CH3:28])([CH3:27])[CH3:26]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 8201511,2-Dihydro-2,7-naphthyridin-1-oneHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 86700141(S)-ethyl 2-(2-bromo-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetate

Product 1

HCID 86700191(S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(1-oxo-2,7-naphthyridin-2(1H)-yl)benzo[d]thiazol-6-yl)acetate

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of (S)-ethyl 2-(2-bromo-7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl)-2-tert-butoxyacetate (36.7 mg, 0.076 mmol) and 2,7-naphthyridin-1(2H)-one (14.0 mg, 0.092 mmol) in DMF (0.9 mL) was added CuI (9.0 mg, 0.046 mmol) and trans-N1,N2-dimethylcyclohexane-1,2-diamine (15 μL, 0.092 mmol) and K2CO3 (21.0 mg, 0.152 mmol). The reaction was heated at 110° C. for 2 h. After cooling, the reaction mixture was diluted with EtOAc, extracted with H2O, brine, dried over Na2SO4, filtered and concentrated and purified by flash column chromatography (silica gel, 0 to 100% ethyl acetate/hexanes) to give the desired product. LCMS-ESI+ (m/z): [M+H]+ calcd for C30H29ClN3O4S: 562.2; found: 562.3.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with H2O, brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by flash column chromatography (silica gel, 0 to 100% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-555d933074ff4c19a9a4e5636c43f1f1
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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