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Glycolic Acid → 2-hydroxy-N-methyl-N-(2-{[4-({3-methyl-4-[(6-methylpyridin-3-yl)oxy]phenyl}amino)quinazolin-5-yl]oxy}ethyl)acetamide

HRID 1864352
ノート
印刷プレビュー

反応式

HRID 1864352 の反応式
[CH3:1][NH:2][CH2:3][CH2:4][O:5][C:6]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:7]=1[C:8]([NH:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][C:24]3[CH:25]=[N:26][C:27]([CH3:30])=[CH:28][CH:29]=3)=[C:19]([CH3:31])[CH:18]=1)=[N:9][CH:10]=[N:11]2.[C:32]([OH:36])(=O)[CH2:33][OH:34].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CC(N(C)C)=O>[OH:34][CH2:33][C:32]([N:2]([CH3:1])[CH2:3][CH2:4][O:5][C:6]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:7]=1[C:8]([NH:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][C:24]3[CH:25]=[N:26][C:27]([CH3:30])=[CH:28][CH:29]=3)=[C:19]([CH3:31])[CH:18]=1)=[N:9][CH:10]=[N:11]2)=[O:36]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 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 690582265-[2-(Methylamino)ethoxy]-N-{3-methyl-4-[(6-methylpyridin-3-yl)oxy]phenyl}quinazolin-4-amine

生成物 1

HCID 112252522-hydroxy-N-methyl-N-(2-{[4-({3-methyl-4-[(6-methylpyridin-3-yl)oxy]phenyl}amino)quinazolin-5-yl]oxy}ethyl)acetamide収率 60.3%

試薬・触媒・溶媒

1
HCID 31374Dimethylacetamide溶媒

実験手順

5-[2-(Methylamino)ethoxy]-N-{3-methyl-4-[(6-methylpyridin-3-yl)oxy]phenyl}quinazolin-4-amine (32 mg, 0.077 mmol) and glycolic acid (6 mg, 0.085 mmol) were dissolved in DMA (10 ml). HATU (32 mg, 0.085 mmol) was added, and the mixture was stirred at ambient temperature for 16 hours. The mixture was concentrated in vacuo, and the residue purified by reverse-phase HPLC, eluting with 5 to 50% acetonitrile in H2O containing 0.2% TFA. The appropriate fraction was evaporated, and the residue dissolved in methanol/DCM (1:1, 25 ml). The mixture was neutralised by stirring overnight with tetraalkylammonium carbonate, polymer bound. The mixture was filtered, and the filtrate was evaporated. Crystallisation from ethyl acetate/iso-hexane gave 2-hydroxy-N-methyl-N-(2-{[4-({3-methyl-4-[(6-methylpyridin-3-yl)oxy]phenyl}amino)quinazolin-5-yl]oxy}ethyl)acetamide as a white crystalline solid (22 mg, 60%); NMR Spectrum (DMSO-d6, 400 MHz, 373K) 2.26 (s, 3H), 2.48 (s, 3H), 3.02 (s, 3H), 3.95 (t, 2H), 4.02-4.11 (m-3H), 4.55 (t, 2H), 6.96 (d, 1H), 7.20 (d, 1H), 7.23 (m, 2H), 7.38 (d, 1H), 7.65 (dd, 1H), 7.70 (d, 1H), 7.73 (dd, 1H), 8.20 (m, 1H), 8.49 (s, 1H), 9.77 (s, 1H); Mass spectrum MH+ 473.9

後処理

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue purified by reverse-phase HPLC
  3. washeluting with 5 to 50% acetonitrile in H2O containing 0.2% TFA
  4. customThe appropriate fraction was evaporated
  5. dissolutionthe residue dissolved in methanol/DCM (1:1, 25 ml)
  6. stirringby stirring overnight with tetraalkylammonium carbonate, polymer
  7. filtrationThe mixture was filtered
  8. customthe filtrate was evaporated
  9. customCrystallisation from ethyl acetate/iso-hexane

出典と根拠

ORDレコード
ord-7c90c72ddf4143be9e1f668a6f58058d
出典データセット
uspto-grants-2009_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07625908B2

反応ノート

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