Cesium carbonate → HCID 24896736, compound

HRID 1819880Notes

Reaction equation

HRID 1819880 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[CH:19]=[CH:18][C:9]2[O:10][C:11]3[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][C:12]=3[C:8]=2[CH:7]=1)=[O:4].[CH3:20][N:21]([CH3:26])[CH2:22][CH2:23][NH:24][CH3:25].C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[CH3:20][N:21]([CH3:26])[CH2:22][CH2:23][N:24]([CH3:25])[CH2:2][C:3]([NH:5][C:6]1[CH:19]=[CH:18][C:9]2[O:10][C:11]3[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][C:12]=3[C:8]=2[CH:7]=1)=[O:4]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 673381,2-Ethanediamine, N1,N1,N2-trimethyl-HCID 24900205HCID 24900205, compound

Product 1

HCID 24896736HCID 24896736, compoundYield 37.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Following the procedure of Example 40, 2-chloro-N-7,8,9,10-tetrahydro-6H-benzo[b]cyclohepta[d]furan-2-ylacetamide (0.13 g, 0.45 mmol), N,N,N′-trimethylethylenediamine (0.073 mL, 0.56 mmol), and cesium carbonate (0.29 g, 0.90 mmol) in acetonitrile (5 mL) provided N2-[2-(dimethylamino)ethyl]-N2-methyl-N1-7,8,9,10-tetrahydro-6H-benzo[b]cyclohepta[d]furan-2-ylglycinamide (0.058 g) as its hydrochloride salt after normal phase HPLC purification and treatment with 4 N hydrochloric acid in dioxane. MS (ESI) m/z 344 ([M+H]+).

Sources & evidence

ORD record
ord-9e6644c86402451b9e439d0d8cc14076
Source dataset
uspto-grants-2009_10
Patent number
US07601856B2

Reaction notes

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