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Dichloromethane → 3-Methoxy-4-(6-(methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino)pyridazin-3-yl)benzoic acid

HRID 1027164
ノート
印刷プレビュー

反応式

HRID 1027164 の反応式
Cl[C:2]1[N:7]=[N:6][C:5]([N:8]([CH3:19])[CH:9]2[CH2:14][C:13]([CH3:16])([CH3:15])[NH:12][C:11]([CH3:18])([CH3:17])[CH2:10]2)=[CH:4][CH:3]=1.B([C:23]1[CH:31]=[CH:30][C:26]([C:27]([OH:29])=[O:28])=[CH:25][C:24]=1[O:32][CH3:33])(O)O.C(Cl)Cl.C([O-])([O-])=O.[Na+].[Na+]>O.CCOCC.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].CN(C=O)C>[CH3:33][O:32][C:24]1[CH:25]=[C:26]([CH:30]=[CH:31][C:23]=1[C:2]1[N:7]=[N:6][C:5]([N:8]([CH3:19])[CH:9]2[CH2:14][C:13]([CH3:16])([CH3:15])[NH:12][C:11]([CH3:18])([CH3:17])[CH2:10]2)=[CH:4][CH:3]=1)[C:27]([OH:29])=[O:28]
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

9

反応物 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 231342764-Borono-3-methoxybenzoic acidHCID 867105396-chloro-N-methyl-N-(2,2,6,6-tetramethylpiperidin-4-yl)pyridazin-3-amine2 回

生成物 1

HCID 867105563-Methoxy-4-(6-(methyl-(2,2,6,6-tetramethylpiperidin-4-yl)amino)pyridazin-3-yl)benzoic acid

試薬・触媒・溶媒 4

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
触媒
HCID 962Water溶媒2 回
HCID 3283Diethyl Ether溶媒
HCID 6228Dimethylformamide溶媒

反応条件

温度
120 °C

実験手順

To a microwave vial was added 6-chloro-N-methyl-N-(2,2,6,6-tetramethylpiperidin-4-yl)pyridazin-3-amine (Intermediate 1-1, 100 mg, 0.35 mmol), 4-borono-3-methoxybenzoic acid (76 mg, 0.39 mmol), PdCl2(dppf).CH2Cl2 (29 mg, 0.035 mmol), Na2CO3 (112 mg, 1.06 mmol), DMF (2 mL) and water (0.5 mL). The microwave vial was sealed and heated in a microwave at 120° C. for 45 min. The crude reaction mixture was cooled and diluted in water and ether. The aqueous layer was extracted with ether. The resultant emulsion was diluted in water and 1 M NaOH. The aqueous layer was acidified with 1 M HCl slowly and extracted again with ether. The organic layer was concentrated under reduced pressure, and the resulting precipitate was suspended in 10 mL MeOH and filtered. The filtrate was concentrated and used without further purification. LCMS Rt=0.63 min (condition B); MS (M+1)=399.0

後処理

  1. customThe microwave vial was sealed
  2. customThe crude reaction mixture
  3. temperaturewas cooled
  4. extractionThe aqueous layer was extracted with ether
  5. additionThe resultant emulsion was diluted in water
  6. extractionextracted again with ether
  7. concentrationThe organic layer was concentrated under reduced pressure
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated
  10. customused without further purification

出典と根拠

ORDレコード
ord-667e7c1fe362406597737c664f7e9bb2
出典データセット
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08729263B2

反応ノート

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