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

HRID 2080194
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HRID 2080194 반응식
[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]
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참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 6422Trifluoroacetic acid용매2회
HCID 18373917Acetonitrile--water (1/1)용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-376b8d55c61b4035bd839f7f123ae4b5
출처 데이터셋
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07932272B2

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