Tetrahydrofuran → 2-Amino-6-(3-methoxy-propyl)-N-(5-phenoxy-thiophen-2-ylmethyl)-nicotinamide

HRID 2080208Notes

Reaction equation

HRID 2080208 reaction equation
[NH2:1][C:2]1[N:23]=[C:22](/[CH:24]=[CH:25]\[CH2:26][O:27][CH3:28])[CH:21]=[CH:20][C:3]=1[C:4]([NH:6][CH2:7][C:8]1[S:9][C:10]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:11][CH:12]=1)=[O:5].O1CCCC1.C(N(CC)CC)C>C(#N)C.O.FC(F)(F)C(O)=O.[C].[Pd]>[NH2:1][C:2]1[N:23]=[C:22]([CH2:24][CH2:25][CH2:26][O:27][CH3:28])[CH:21]=[CH:20][C:3]=1[C:4]([NH:6][CH2:7][C:8]1[S:9][C:10]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:11][CH:12]=1)=[O:5]

Participants

7

Reactant 3

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 583879142-Amino-6-(3-methoxy-1-(Z)-propenyl)-N-(5-phenoxy-thiophen-2-ylmethyl)-nicotinamide

Product 1

HCID 231303662-Amino-6-(3-methoxy-propyl)-N-(5-phenoxy-thiophen-2-ylmethyl)-nicotinamideYield 16%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 6422Trifluoroacetic acidSolvent2×HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

To a mixture of 2-amino-6-(3-methoxy-1-(Z)-propenyl)-N-(5-phenoxy-thiophen-2-ylmethyl)-nicotinamide described in Example A-90 (3.0 mg, 0.0059 mmol) and tetrahydrofuran (1 mL) were added triethylamine (3.6 mg, 0.036 mmol) and 10% palladium-carbon (50% water wet, 5 mg), and the solution was stirred under hydrogen atmosphere at room temperature for 15 minutes. The interior of the reaction system was exchanged with nitrogen, then, filtration was carried out through Celite pad, the solvent was evaporated in vacuo. The residue was purified by reverse phase high performance liquid chromatography (acetonitrile-water mobile phase (containing 0.1% trifluoroacetic acid) was used), and trifluoroacetic acid salt of the title compound (0.48 mg, 0.00094 mmol, 16%) was obtained.

Workup

  1. filtrationfiltration
  2. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-46c8836fefbb407a8717276008087eb5
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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