Glycolic Acid → 2-Hydroxy-N-[2-({4-[4-hydroxy-3-methylanilino]quinazolin-5-yl}oxy)ethyl]-N-methylacetamide

HRID 1864192노트

반응식

HRID 1864192 반응식
[C:1]([OH:5])(=O)[CH2:2][OH:3].[CH3:6][C:7]1[CH:12]=[C:11]([NH:13][C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][C:22]=3[O:24][CH2:25][CH2:26][NH:27][CH3:28])[N:17]=[CH:16][N:15]=2)[CH:10]=[CH:9][C:8]=1[OH:29].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[OH:3][CH2:2][C:1]([N:27]([CH2:26][CH2:25][O:24][C:22]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:23]=1[C:14]([NH:13][C:11]1[CH:10]=[CH:9][C:8]([OH:29])=[C:7]([CH3:6])[CH:12]=1)=[N:15][CH:16]=[N:17]2)[CH3:28])=[O:5]

참가 물질

5

반응물 3

HCID 757Glycolic AcidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 690540072-Methyl-4-({5-[2-(methylamino)ethoxy]quinazolin-4-yl}amino)phenol

생성물 1

HCID 690579972-Hydroxy-N-[2-({4-[4-hydroxy-3-methylanilino]quinazolin-5-yl}oxy)ethyl]-N-methylacetamide수율 86.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매3회

실험 절차

A solution of glycolic acid (100 mg) in DMF (2 ml) was added dropwise to a solution of 2-methyl-4-({5-[2-(methylamino)ethoxy]quinazolin-4-yl}amino)phenol (400 mg) in DMF (4 ml) and the mixture held under sonication for 5 minutes. A solution of HATU (519 mg) in DMF (2 ml) was then added and the solution was stirred at ambient temperature for 16 hours, and then concentrated in vacuo. The residue was treated with water to precipitate a brown solid that was collected by filtration, and washed with water to give 2-hydroxy-N-[2-({4-[4-hydroxy-3-methylanilino]quinazolin-5-yl}oxy)ethyl]-N-methylacetamide as a brown solid (406 mg, 86%); NMR spectrum (DMSO-d6) 2.15 (s, 3H), 2.94 (s, 3H), 3.87 (m, 2H), 4.04 (s, 2H), 4.48 (m, 2H), 6.81 (d, 1H), 7.20 (dd, 1H), 7.25 (d, 1H), 7.35 (m, 2H), 7.92 (t, 1H), 8.64 (s, 1H), 9.46 (s, 1H), 10.49 (s, 1H); Mass spectrum M+ 383.

후처리

  1. customthe mixture held under sonication for 5 minutes
  2. concentrationconcentrated in vacuo
  3. additionThe residue was treated with water
  4. customto precipitate a brown solid
  5. filtrationthat was collected by filtration
  6. washwashed with water

출처 및 근거

ORD 기록
ord-a3c792961d67464e84e2030467c14ad2
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07625908B2

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