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1,4-Dioxane → 1-(1-(5,6-dimethylpyrazin-2-yl)piperidin-4-yl)-N,N-dimethyl-2',3'-dihydrospiro[piperidine-4,4'-quinoline]-1'-carboxamide

HRID 2382992
ノート
印刷プレビュー

反応式

HRID 2382992 の反応式
CC(C)([O-])C.[Na+].O1CCOCC1.[CH3:13][N:14]([CH3:38])[C:15]([N:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:20]2([CH2:31][CH2:30][N:29]([CH:32]3[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]3)[CH2:28][CH2:27]2)[CH2:19][CH2:18]1)=[O:16].Cl[C:40]1[N:41]=[C:42]([CH3:47])[C:43]([CH3:46])=[N:44][CH:45]=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C(Cl)(Cl)Cl.CC#N>[CH3:47][C:42]1[N:41]=[CH:40][C:45]([N:35]2[CH2:36][CH2:37][CH:32]([N:29]3[CH2:28][CH2:27][C:20]4([C:21]5[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=5)[N:17]([C:15]([N:14]([CH3:38])[CH3:13])=[O:16])[CH2:18][CH2:19]4)[CH2:31][CH2:30]3)[CH2:33][CH2:34]2)=[N:44][C:43]=1[CH3:46]
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 312751,4-DioxaneHCID 126003905-Chloro-2,3-dimethylpyrazineHCID 23676156Sodium t-butoxideHCID 24798103N,N-dimethyl-1-(piperidin-4-yl)-2',3'-dihydrospiro[piperidine-4,4'-quinoline]-1'-carboxamide

生成物 1

HCID 236517101-(1-(5,6-dimethylpyrazin-2-yl)piperidin-4-yl)-N,N-dimethyl-2',3'-dihydrospiro[piperidine-4,4'-quinoline]-1'-carboxamide

試薬・触媒・溶媒 2

HCID 11029508Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1)触媒HCID 6342Acetonitrile溶媒

反応条件

温度
80 °C

実験手順

Pd2(dba)3-CHCl3 (5 mg, 0.5 mol %), ligand 1 (8 mg, 2 mol %) and 1.4 eq sodium tert-butoxide (13 mg, 0.14 mmol) were weighed in air and transferred into a microwave tube, followed by dioxane (750 μL), 1.0 eq N,N-dimethyl-1-(piperidin-4-yl)-2′H-spiro[piperidine-4,4′-quinoline]-1′(3′H)-carboxamide (36 mg, 0.10 mmol) and 1.0 eq 5-chloro-2,3-dimethylpyrazine (14 mg). The tube was flushed with nitrogen, capped and stirred at 80° C. for 3 hours. The reaction was cooled to room temperature, diluted with methanol (500 μL), filtered (Whatman 0.45 μm PTFE) and subjected to reverse-phase HPLC purification (2-40% CH3CN gradient [w/0.1% TFA (aq)] over t=10 minutes, 750 μL injected, 35 mL/min) to yield compound no. 20. LC/MS (10-99% CH3CN/0.05% TFA gradient over 5 min): m/z 463.4, retention time 2.13 minutes.

後処理

  1. customtransferred into a microwave tube
  2. customThe tube was flushed with nitrogen
  3. customcapped
  4. temperatureThe reaction was cooled to room temperature
  5. additiondiluted with methanol (500 μL)
  6. filtrationfiltered (Whatman 0.45 μm PTFE)
  7. customsubjected to reverse-phase HPLC purification (2-40% CH3CN gradient [w/0.1% TFA (aq)] over t=10 minutes, 750 μL injected, 35 mL/min)
  8. customto yield compound no

出典と根拠

ORDレコード
ord-73f0c82dd4c8472d9903265ffd7f2dc5
出典データセット
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08263605B2

反応ノート

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