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

HRID 2080194
ノート
印刷プレビュー

反応式

HRID 2080194 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6422Trifluoroacetic acid溶媒2 回
HCID 18373917Acetonitrile--water (1/1)溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-376b8d55c61b4035bd839f7f123ae4b5
出典データセット
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07932272B2

反応ノート

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