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Ethanolamine → N-(2-hydroxyethyl)-1-[(6-methoxy-5-methyl-pyrimidin-4-yl)methyl]pyrrolo[3,2-b]pyridine-3-carboxamide

HRID 1753233
ノート
印刷プレビュー

反応式

HRID 1753233 の反応式
[CH3:1][O:2][C:3]1[N:8]=[CH:7][N:6]=[C:5]([CH2:9][N:10]2[C:18]3[C:13](=[N:14][CH:15]=[CH:16][CH:17]=3)[C:12]([C:19]([OH:21])=O)=[CH:11]2)[C:4]=1[CH3:22].C(N(CC)CC)C.CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O.[CH2:48]([CH2:50][NH2:51])[OH:49]>C(Cl)Cl>[OH:49][CH2:48][CH2:50][NH:51][C:19]([C:12]1[C:13]2=[N:14][CH:15]=[CH:16][CH:17]=[C:18]2[N:10]([CH2:9][C:5]2[C:4]([CH3:22])=[C:3]([O:2][CH3:1])[N:8]=[CH:7][N:6]=2)[CH:11]=1)=[O:21]
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 4

HCID 700EthanolamineHCID 8471TriethylamineHCID 111923Propylphosphonic anhydrideHCID 1178190601-((6-methoxy-5-methylpyrimidin-4-yl)methyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxylic acid

生成物 1

HCID 72792765N-(2-hydroxyethyl)-1-[(6-methoxy-5-methyl-pyrimidin-4-yl)methyl]pyrrolo[3,2-b]pyridine-3-carboxamide収率 45%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

See FIG. 18(a). 1-((6-methoxy-5-methylpyrimidin-4-yl)methyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxylic acid (1 g, 3.35 mmol) was taken in DCM (20 mL) to get a suspension. Triethyl amine (1.394 mL, 10.06 mmol) was added followed by the addition of 1-Propanephosphonic acid cyclic anhydride (3.991 mL, 6.70 mmol). The reaction mass was stirred at RT for 5 minutes. Ethanol amine (6.02 mL, 10.06 mmol) was added and stirred at RT for 2 h. After completion of the reaction, diluted with DCM and then washed with water and brine solution. The organic layer was separated, dried, evaporated and the crude compound was purified by silica gel chromatography. Yield-45%. ES+MS m/z: 342 (M+1). 1H NMR (300 MHz, DMSO-d6) δ ppm 2.24 (s. 3 H ) 3.37-3.64 (m, 4 H ) 3.94 (s, 3 H ) 4.80 (t, J=4.99 Hz, 1 H ) 5.67 (s, 2 H ) 7.24 (dd, J=8.29, 4.52 Hz, 1 H ) 7.92 (d, J=8.10 Hz, 1 H ) 8.23 (s, 1 H ) 8.41 (s, 1 H ) 8.47 (d, J=4.52 Hz, 1 H ) 8.85 (t, J=5.37 Hz, 1 H ).

後処理

  1. customto get a suspension
  2. stirringstirred at RT for 2 h
  3. customAfter completion of the reaction
  4. washwashed with water and brine solution
  5. customThe organic layer was separated
  6. customdried
  7. customevaporated
  8. customthe crude compound was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-2dc9c79f37544640a915afcc62ef0713
出典データセット
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09163020B2

反応ノート

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