Sodium methanethiolate → HCID 16065392、化合物

HRID 2425515ノート

反応式

HRID 2425515 の反応式
Br[CH2:2][C:3]1[C:4]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[N:5][C:6]2[C:11]([C:12]=1[C:13]([NH:15][C@H:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:17][CH3:18])=[O:14])=[CH:10][CH:9]=[CH:8][CH:7]=2.[CH3:31][S-:32].[Na+]>C1COCC1.CCOC(C)=O>[CH3:31][S:32][CH2:2][C:3]1[C:4]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[N:5][C:6]2[C:11]([C:12]=1[C:13]([NH:15][C@H:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:17][CH3:18])=[O:14])=[CH:10][CH:9]=[CH:8][CH:7]=2

参加物

5

反応物 2

HCID 4378561Sodium methanethiolateHCID 16064396HCID 16064396、化合物

生成物 1

HCID 16065392HCID 16065392、化合物収率 92.7%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a stirring solution of 3-(bromomethyl)-2-phenyl-N-[(1S)-1-phenylpropyl]quinoline-4-carboxamide (8) (2.9 g, 6.32 mmol) in anhydrous THF (35 mL) under N2 was added sodium thiomethoxide (NaSMe, 880 mg, 12.64 mmol) and reaction stirred 1.5 h. It was then diluted with EtOAc; washed with aqueous 0.3 N NaOH, then H2O, then brine; dried over Na2SO4; filtered; and concentrated under reduced pressure. The residue was purified by silica gel chromatography (5-15% EtOAc/CH2Cl2) to give the desired product (2.5 g, 90% yield) as a solid. 1H NMR (300 MHz, CDCl3, 52° C.) δ 8.10 (d, J=8.4 Hz, 1H), 7.78 (d, J=8.1 Hz, 1H), 7.72-7.60 (m, 3H), 7.53-7.25 (m, 9H), 6.68 (d, J=7.8 Hz, 1H), 5.29 (q, J=7.6 Hz, 1H), 3.79 (q, J=13.7 Hz, 2H), 2.19-1.90 (m, 2H), 1.77 (s, 3H), 1.03 (t, J=7.4 Hz, 3H); LCMS: m/z 427 (MH+).

後処理

  1. washwashed with aqueous 0.3 N NaOH
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationand concentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography (5-15% EtOAc/CH2Cl2)

出典と根拠

ORDレコード
ord-361c89fa2d8d4921877c0432a69cf5e0
出典データセット
uspto-grants-2011_06
特許番号
US07964733B2

反応ノート

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