Betahistine → HCID 24896737, compound

HRID 1819881Notes

Reaction equation

HRID 1819881 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][NH:21][CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=1.C(=O)([O-])[O-].[Cs+].[Cs+].FC(F)(F)C(O)=O>C(#N)C>[CH3:20][N:21]([CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=1)[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

6

Reactant 4

HCID 2366BetahistineHCID 6422Trifluoroacetic acidHCID 10796Cesium carbonateHCID 24900205HCID 24900205, compound

Product 1

HCID 24896737HCID 24896737, compoundYield 55.9%

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), 2-(2-methylaminoethyl)pyridine (0.078 mL, 0.56 mmol), and cesium carbonate (0.29 g, 0.90 mmol) in acetonitrile (5 mL) provided N2-methyl-N2-(2-pyridin-2-ylethyl)-N1-7,8,9,10-tetrahydro-6H-benzo[b]cyclohepta[d]furan-2-ylglycinamide (0.095 g) as its trifluroacetic acid salt after reverse-phase HPLC purification.MS (ESI) m/z 378 ([M+H]+).

Sources & evidence

ORD record
ord-062eb7e9002e496d9ce45cad8bb035e7
Source dataset
uspto-grants-2009_10
Patent number
US07601856B2

Reaction notes

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