Cesium carbonate → HCID 57933062, compound

HRID 1432709Notes

Reaction equation

HRID 1432709 reaction equation
[Cl:1][C:2]1[CH:6]=[C:5](I)[S:4][C:3]=1[C:8]1[N:12]2[N:13]=[C:14]([CH3:22])[CH:15]=[C:16]([CH:17]([CH2:20][CH3:21])[CH2:18][CH3:19])[C:11]2=[N:10][C:9]=1[CH3:23].N1C=[CH:27][N:26]=[N:25]1.C([O-])([O-])=O.[Cs+].[Cs+].[CH3:35][NH:36][C@H]1CCCC[C@@H]1NC>C(Cl)Cl.[Cu]I.CN(C=O)C>[Cl:1][C:2]1[CH:6]=[C:5]([N:26]2[CH:27]=[N:36][CH:35]=[N:25]2)[S:4][C:3]=1[C:8]1[N:12]2[N:13]=[C:14]([CH3:22])[CH:15]=[C:16]([CH:17]([CH2:20][CH3:21])[CH2:18][CH3:19])[C:11]2=[N:10][C:9]=1[CH3:23]

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 13822957(1S,2S)-(+)-N,N'-Dimethylcyclohexane-1,2-diamineHCID 68840906HCID 68840906, compoundHCID 178418936HCID 178418936, compound

Product 1

HCID 57933062HCID 57933062, compoundYield 71.4%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
112 °C

Procedure

To a solution of 3-(3-chloro-5-iodo-thiophen-2-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine (0.30 g, 0.65 mmol), 1H-triazole (0.047 g, 0.69 mmol), CuI (0.0062, 0.033 mmol), Cs2CO3 (0.45 g, 1.37 mmol) and DMF (3 mL) is added (1S,2S)-(+)-N,N′-dimethylcyclohexane-1,2-diamine (0.014 mL, 0.098 mmol). The solution is heated at 112° C. overnight, diluted with CH2Cl2 (10 mL) and filtered thru Celite® and concentrated. The residue is purified by ISCO flash chromatography (30%-40% EtOAc gradient furnish the title compound (0.028 g, 0.070 mmol, 11%). 1H NMR (CDCl3) δ 0.87 (t, J=7.5 Hz, 6H), 1.75-1.92 (m, 4H), 2.51 (s, 3H), 2.52 (s, 3H), 3.26-3.35 (m, 1H), 6.72 (s, 1H), 7.22 (s, 1H), 8.10 (s, 1H), 8.50 (s, 1H). LC/MS (m/z): calcd. for C19H21ClN6S (M+H)+: 401.1; found: 401.2.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. customThe residue is purified by ISCO flash chromatography (30%-40% EtOAc gradient

Sources & evidence

ORD record
ord-f0f22e15d5ad405fbef8c4cf7f4c1086
Source dataset
uspto-grants-2009_11
Patent number
US07612067B2

Reaction notes

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