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Potassium Phosphate, Tribasic → 3-{[(Benzyloxy)carbonyl]amino}-7-(4-methyl-3-oxopiperazin-1-yl)quinoline-2-carboxylic acid

HRID 924485
ノート
印刷プレビュー

反応式

HRID 924485 の反応式
[CH2:1]([O:8][C:9]([NH:11][C:12]1[C:13]([C:23]([O:25]CC)=[O:24])=[N:14][C:15]2[C:20]([CH:21]=1)=[CH:19][CH:18]=[C:17](Br)[CH:16]=2)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:28][N:29]1[CH2:34][CH2:33][NH:32][CH2:31][C:30]1=[O:35].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC(C)C)=CC=CC=2OC(C)C)CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C(O)(C)(C)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH2:1]([O:8][C:9]([NH:11][C:12]1[C:13]([C:23]([OH:25])=[O:24])=[N:14][C:15]2[C:20]([CH:21]=1)=[CH:19][CH:18]=[C:17]([N:32]1[CH2:33][CH2:34][N:29]([CH3:28])[C:30](=[O:35])[CH2:31]1)[CH:16]=2)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=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 62657Potassium Phosphate, TribasicHCID 43990421-Methylpiperazin-2-oneHCID 162179852-Dicyclohexylphosphino-2',6'-diisopropoxybiphenylHCID 86726857Ethyl 3-(((benzyloxy)carbonyl)amino)-7-bromoquinoline-2-carboxylate

生成物 1

HCID 867269303-{[(Benzyloxy)carbonyl]amino}-7-(4-methyl-3-oxopiperazin-1-yl)quinoline-2-carboxylic acid収率 9.5%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 6386tert-Butanol溶媒

反応条件

温度
100 °C

実験手順

A mixture of ethyl 3-{[(benzyloxy)carbonyl]amino}-7-bromoquinoline-2-carboxylate (250 mg, 0.58 mmol), 1-methylpiperazin-2-one (130 mg, 1.2 mmol), Pd(OAc)2 (20 mg), dicyclohexyl(2′,6′-diisopropoxybiphenyl-2-yl)phosphine (41 mg, 0.087 mmol), and K3PO4 (490 mg, 2.3 mmol) in tert-butyl alcohol (8 mL) was purged with nitrogen then heated at 100° C. in a sealed vial for 3 h. The mixture was then allowed to cool and EtOAc and water were added. The resulting layers were separated and organic layer was concentrated under reduced pressure. To the resulting bright-yellow solid, 2 mL of dioxane, 2 mL of 2 M NaOH were added. The mixture was heated in 80° C. oil bath with stirring for 0.5 h, then allowed to cooled and neutralized with 4 mL of with 1 M HCl. The red solid formed was collected by filtration and air-dried overnight to give the sub-title compound (24 mg, 9.5%). LCMS calc. for C26H33N8O2 [M+H]+: m/z=489.3. found: 435.2.

後処理

  1. customwas purged with nitrogen
  2. temperatureto cool
  3. additionEtOAc and water were added
  4. customThe resulting layers were separated
  5. concentrationorganic layer was concentrated under reduced pressure
  6. additionTo the resulting bright-yellow solid, 2 mL of dioxane, 2 mL of 2 M NaOH were added
  7. temperatureThe mixture was heated in 80° C. oil bath
  8. temperatureto cooled
  9. customThe red solid formed
  10. filtrationwas collected by filtration
  11. customair-dried overnight

出典と根拠

ORDレコード
ord-7bfa183977c545eda4a7f7e17ae8994f
出典データセット
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09278950B2

反応ノート

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