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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
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HRID 1753233 반응식
[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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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 ).

후처리

  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

출처 및 근거

ORD 기록
ord-2dc9c79f37544640a915afcc62ef0713
출처 데이터셋
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09163020B2

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