Quinoline → 2-Amino-6-(3-methoxy-1-(Z)-propenyl)-N-(5-phenoxy-thiophen-2-ylmethyl)-nicotinamide

HRID 2080194Notes

Reaction equation

HRID 2080194 reaction equation
[NH2:1][C:2]1[N:23]=[C:22]([C:24]#[C: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.N1C2C(=CC=CC=2)C=CC=1>C(#N)C.O.FC(F)(F)C(O)=O>[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]

Participants

6

Reactant 3

HCID 7047QuinolineHCID 8028TetrahydrofuranHCID 231307162-Amino-6-(3-methoxy-1-propynyl)-N-(5-phenoxy-thiophen-2-ylmethyl)-nicotinamide

Product 1

HCID 583879142-Amino-6-(3-methoxy-1-(Z)-propenyl)-N-(5-phenoxy-thiophen-2-ylmethyl)-nicotinamideYield 31%

Reagents, catalysts & solvents 2

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

Procedure

To a mixture of 2-amino-6 (3methoxy-1-propynyl)-N-(5-phenoxy-thiophen-2-yl methyl)-nicotinamide described in Example A-91 (11 mg, 0.028 mmol) and tetrahydrofuran (1 mL) were added quinoline (5.4 mg, 0.042 mmol) and Linear catalyst (5.0 mg), and the mixture 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, and the solvent was evaporated in vacuo. The residue was filtered by NH silica gel, then, 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 (4.4 mg, 0.0086 mmol, 31%) was obtained.

Workup

  1. filtrationfiltration
  2. customthe solvent was evaporated in vacuo
  3. filtrationThe residue was filtered by NH silica gel

Sources & evidence

ORD record
ord-376b8d55c61b4035bd839f7f123ae4b5
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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