Potassium Carbonate → HCID 68905931, compound

HRID 1783497Notes

Reaction equation

HRID 1783497 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[S:18][C:19]3[CH:25]=[C:24](I)[CH:23]=[CH:22][C:20]=3[N:21]=2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:27]1([SH:37])[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:30]=[CH:29][CH:28]=1.C([O-])([O-])=O.[K+].[K+]>C(O)(C)C.CO.C(Cl)Cl.[Cu]I>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[S:18][C:19]3[CH:25]=[C:24]([S:37][C:27]4[C:36]5[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=5)[CH:30]=[CH:29][CH:28]=4)[CH:23]=[CH:22][C:20]=3[N:21]=2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 682591-NaphthalenethiolHCID 68834936HCID 68834936, compound

Product 1

HCID 68905931HCID 68905931, compound

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 887MethanolSolventHCID 3776IsopropanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 4-(6-iodobenzothiazol-2-yl)piperazine-1-carboxylic acid benzyl ester (0.370 g, 0.77 mmol), 1-napthalenethiol (0.124 g, 0.77 mmol), CuI (0.015 g, 0.08 mmol), and K2CO3 (0.213 g, 0.77 mmol) in isopropanol was heated at 90° C. overnight, cooled to 25° C., diluted with 20% MeOH in CH2Cl2, and filtered through a pad of silica gel. The filtrate was concentrated in vacuo to provide the title compound which used in Example 41 without further purification.

Workup

  1. temperaturecooled to 25° C.
  2. filtrationfiltered through a pad of silica gel
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-0e0b81e8b38c4a44917d8ddedd10f6bd
Source dataset
uspto-grants-2009_03
Patent number
US07501421B2

Reaction notes

Loading…