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1,2-Dimethoxyethane → 5-[2-Methoxy-4-(4-methylpiperazin-1-yl)phenyl]-3-oxazolo[4,5-b]pyridin-2-yl-pyridin-2-amine

HRID 908393
ノート
印刷プレビュー

反応式

HRID 908393 の反応式
[O:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]=[C:2]1[C:10]1[C:11]([NH2:25])=[N:12][CH:13]=[C:14](B2OC(C)(C)C(C)(C)O2)[CH:15]=1.Br[C:27]1[CH:32]=[CH:31][C:30]([N:33]2[CH2:38][CH2:37][N:36]([CH3:39])[CH2:35][CH2:34]2)=[CH:29][C:28]=1[O:40][CH3:41].C(=O)([O-])[O-].[Na+].[Na+].COCCOC>[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>[CH3:41][O:40][C:28]1[CH:29]=[C:30]([N:33]2[CH2:34][CH2:35][N:36]([CH3:39])[CH2:37][CH2:38]2)[CH:31]=[CH:32][C:27]=1[C:14]1[CH:15]=[C:10]([C:2]2[O:1][C:9]3[C:4]([N:3]=2)=[N:5][CH:6]=[CH:7][CH:8]=3)[C:11]([NH2:25])=[N:12][CH:13]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 673878191-(4-Bromo-3-methoxyphenyl)-4-methylpiperazineHCID 673889723-Oxazolo[4,5-b]pyridin-2-yl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine

生成物 1

HCID 673881955-[2-Methoxy-4-(4-methylpiperazin-1-yl)phenyl]-3-oxazolo[4,5-b]pyridin-2-yl-pyridin-2-amine収率 55.1%

試薬・触媒・溶媒 2

HCID 6102075Dichlorobis(triphenylphosphine)palladium触媒HCID 962Water溶媒

反応条件

温度
100 °C

実験手順

Compound [6] was prepared as follows. 3-oxazolo[4,5-b]pyridin-2-yl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine (138 mg), 1-(4-bromo-3-methoxy-phenyl)-4-methyl-piperazine (97 mg), bis(triphenylphosphine) palladium (II) chloride (50.1 mg) and sodium carbonate (50.5 mg) were weighed out and sealed in a tube. DME (3 ml) and water (0.3 ml) were added. Argon was bubbled in the resulting mixture for 10 minutes then it was stirred at 100° C. for 1 hour. After cooling, the reaction mixture was diluted with ethyl acetate (5 ml), filtered, and purified by flash chromatography on silica gel eluting with 0 to 5% methanol in dichloromethane/ethyl acetate (1/1) then 5% methanolic ammonia 7N in dichloromethane/ethyl acetate (1/1). The solvent was evaporated to dryness and the product was triturated in acetonitrile (4 ml), collected by filtration, washed with Acetonitrile and dried under vacuum at 40° C., to give 5-[2-methoxy-4-(4-methylpiperazin-1-yl)phenyl]-3-oxazolo[4,5-b]pyridin-2-yl-pyridin-2-amine (78 mg). NMR Spectrum: (CDCl3) 2.40 (s, 3H), 2.61-2.69 (m, 4H), 3.27-3.36 (m, 4H), 3.85 (s, 3H), 6.58 (d, 1H), 6.62 (dd, 1H), 6.91 (bs, 2H), 7.25 (d, 1H), 7.30 (dd, 1H), 7.85 (dd, 1H), 8.46 (d, 1H), 8.47 (d, 1H), 8.56 (dd, 1H); Mass spectrum: M+H+ 417. There was no deprotection step.

後処理

  1. customsealed in a tube
  2. customArgon was bubbled in the resulting mixture for 10 minutes
  3. temperatureAfter cooling
  4. additionthe reaction mixture was diluted with ethyl acetate (5 ml)
  5. filtrationfiltered
  6. custompurified by flash chromatography on silica gel eluting with 0 to 5% methanol in dichloromethane/ethyl acetate (1/1)
  7. customThe solvent was evaporated to dryness
  8. customthe product was triturated in acetonitrile (4 ml)
  9. filtrationcollected by filtration
  10. washwashed with Acetonitrile
  11. customdried under vacuum at 40° C.

出典と根拠

ORDレコード
ord-d85645e57dd440328183529ac49add56
出典データセット
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08017611B2

反応ノート

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