Trifluoroacetic acid → HCID 59556828, compound

HRID 1172997Notes

Reaction equation

HRID 1172997 reaction equation
[OH-].[Na+].[CH2:3](Br)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[H-].[Na+].F[C:14](F)(F)[C:15]([OH:17])=O.[NH:20]1[CH:24]=[CH:23][N:22]=[C:21]1[CH:25]=O.[C:27]([BH3-])#[N:28].[Na+]>CO.CN(C)C=O.[Cl-].[Zn+2].[Cl-]>[CH2:3]([O:17][C:15]1[CH:14]=[C:27]2[C:5]([CH2:6][CH2:7][CH2:8][N:28]2[CH2:25][C:21]2[NH:22][CH:23]=[CH:24][N:20]=2)=[CH:4][CH:3]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

10

Reactant 6

HCID 6422Trifluoroacetic acidHCID 7498Benzyl BromideHCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 249551H-imidazole-2-carbaldehydeHCID 5003444Sodium cyanoborohydride

Product 1

HCID 59556828HCID 59556828, compound

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 887MethanolSolvent2×HCID 6228DimethylformamideSolvent

Procedure

Analogously to Example 37, the above compound was obtained from 1,2,3,4-tetrahydro-quinolin-7-ol, di-tert-butyldicarbonate and triethylamine in dichloromethane, then treatment with sodium hydroxide in methanol, then treatment with benzyl bromide and sodium hydride in N,N-dimethylformamide, then treatment with trifluoroacetic acid, then treatment with imidazole-2-carboxaldehyde, zinc chloride and sodium cyanoborohydride in methanol. MS (ISP): 320.0 ([M+H]+).

Sources & evidence

ORD record
ord-790c1f1e9b8741cabfb2646a6dacc900
Source dataset
uspto-grants-2010_11
Patent number
US07834044B2

Reaction notes

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