Cesium carbonate → HCID 24896970, compound

HRID 1819888Notes

Reaction equation

HRID 1819888 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].Cl.Cl.[N:22]1[CH:27]=[CH:26][CH:25]=[N:24][C:23]=1[N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[N:22]1[CH:27]=[CH:26][CH:25]=[N:24][C:23]=1[N:28]1[CH2:33][CH2:32][N:31]([CH2:2][C:3]([NH:5][C:6]2[CH:19]=[CH:18][C:9]3[O:10][C:11]4[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][C:12]=4[C:8]=3[CH:7]=2)=[O:4])[CH2:30][CH2:29]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 116802722-Piperazinylpyrimidine dihydrochlorideHCID 24900205HCID 24900205, compound

Product 1

HCID 24896970HCID 24896970, compoundYield 12.1%

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), 1-(pyrimidyl)piperazine dihydrochloride (0.13, 0.56 mmol), and cesium carbonate (0.58 g, 1.8 mmol) in acetonitrile (5 mL) provided 2-(4-pyrimidin-2-ylpiperazin-1-yl)-N-7,8,9,10-tetrahydro-6H-benzo[b]cyclohepta[d]furan-2-ylacetamide (0.022 g) after purification by flash column chromatography (elution with 3% methanol-1% ammonia-dichloromethane). MS (ES) m/z 406.3 ([M+H]+).

Sources & evidence

ORD record
ord-7262b5d92b254b2992ff04b45595cbaf
Source dataset
uspto-grants-2009_10
Patent number
US07601856B2

Reaction notes

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