Triethylamine → N6-Methyl-4-(3-chloro-4-(((ethylamino)carbonyl)amino)phenoxy)-7-methoxy-6-quinolinecarboxamide

HRID 853584ノート

反応式

HRID 853584 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][C:23]=1[NH:24][C:25]([NH:27][CH2:28][CH3:29])=[O:26])[O:5][C:6]1[C:15]2[C:10](=[CH:11][C:12]([O:19][CH3:20])=[C:13]([C:16]([OH:18])=O)[CH:14]=2)[N:9]=[CH:8][CH:7]=1.CN.CO.[CH2:34]([N:36](CC)CC)C.F[P-](F)(F)(F)(F)F.CN([PH+](N(C)C)N(C)C)C>CN(C)C=O.O.C(OCC)(=O)C>[CH3:34][NH:36][C:16]([C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][C:12]=1[O:19][CH3:20])[N:9]=[CH:8][CH:7]=[C:6]2[O:5][C:4]1[CH:21]=[CH:22][C:23]([NH:24][C:25]([NH:27][CH2:28][CH3:29])=[O:26])=[C:2]([Cl:1])[CH:3]=1)=[O:18]

参加物

8

反応物 4

HCID 8471TriethylamineHCID 22494795Tris(dimethylamino)phosphonium hexafluorophosphateHCID 229369534-(3-Chloro-4-(((ethylamino)carbonyl)amino)phenoxy)-7-methoxy-6-quinolinecarboxylic acidHCID 57454252Monomethylamine methanol

生成物 1

HCID 11553718N6-Methyl-4-(3-chloro-4-(((ethylamino)carbonyl)amino)phenoxy)-7-methoxy-6-quinolinecarboxamide収率 74%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

After dissolving 4-(3-chloro-4-(((ethylamino)carbonyl) amino)phenoxy)-7-methoxy-6-quinolinecarboxylic acid (104 mg, 0.250mmol) in dimethylformamide (3 ml), there were added a 40% methylamine-methanol solution (0.100 ml), triethylamine (0.250 ml) and 1H-1,2,3-benzotriazol-1-yloxy)(tri(dimethylamino)) phosphonium hexafluoro phosphate (221mg, 0.500mmol) in that order at room temperature, and the mixture was stirred for 15 hours. The reaction solution was distributed between ethyl acetate and water, and the organic layer was washed with water and saturated brine and dried over anhydrous magnesium sulfate. After distilling off the solvent, the residue was suspended in ethyl acetate, the suspension was diluted with hexane and the crystals were filtered out and blow-dried to obtain the title compound (79.0 mg, 0.184 mmol, 74%) as white crystals.

後処理

  1. washthe organic layer was washed with water and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. distillationAfter distilling off the solvent
  4. additionthe suspension was diluted with hexane
  5. filtrationthe crystals were filtered out and
  6. customblow-dried

出典と根拠

ORDレコード
ord-ad9f08a5babf4aaea3a6e73be8be413d
出典データセット
uspto-grants-2007_08
特許番号
US07253286B2

反応ノート

読み込み中…