Pyridine → N-(3-tert-butylphenyl)-4-methyl-1-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamide

HRID 2098375

Reaktionsgleichung

Reaktionsgleichung von HRID 2098375
C(C1C=C([NH:11][C:12]([C:14]2(C)[CH2:19][CH2:18][N:17]([C:20](OC(C)(C)C)=O)C[CH2:15]2)=O)C=CC=1)(C)(C)C.C(O[C:33]([N:35]1[CH2:40][CH2:39][C:38]([CH3:44])([C:41]([OH:43])=O)[CH2:37][CH2:36]1)=O)(C)(C)C.[N:45]1C=CC=CC=1.C(Cl)(=O)C(Cl)=O.[C:57]([C:61]1[CH:62]=[C:63]([CH:65]=[CH:66][CH:67]=1)[NH2:64])([CH3:60])([CH3:59])[CH3:58]>CN(C=O)C.ClC(Cl)C.ClCCl>[C:57]([C:61]1[CH:62]=[C:63]([NH:64][C:41]([C:38]2([CH3:44])[CH2:37][CH2:36][N:35]([C:33]3[C:19]4[C:14]([CH3:15])=[CH:12][NH:11][C:18]=4[N:17]=[CH:20][N:45]=3)[CH2:40][CH2:39]2)=[O:43])[CH:65]=[CH:66][CH:67]=1)([CH3:60])([CH3:58])[CH3:59]

Komponenten

9

Edukt 5

HCID 1049PyridineHCID 65578Oxalyl chlorideHCID 793343-tert-ButylanilineHCID 232828481-[(Tert-butoxy)carbonyl]-4-methylpiperidine-4-carboxylic acidHCID 86635224HCID 86635224, Verbindung

Produkt 1

HCID 57920200N-(3-tert-butylphenyl)-4-methyl-1-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamideAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228DimethylformamideKatalysatorHCID 6344DichloromethaneLösungsmittelHCID 63651,1-DichloroethaneLösungsmittel

Versuchsvorschrift

Preparation of tert-Butyl 4-(3-tert-butylphenylcarbamoyl)-4-methylpiperidine-1-carboxylate. To a solution of 1-(tert-butoxycarbonyl)-4-methylpiperidine-4-carboxylic acid (0.30 g, 1.2 mmol), DMF (20 drops), and pyridine (0.38 g, 4.8 mmol) in dichloroethane (10 mL) was added oxalyl chloride (0.15 g, 1.2 mmol). The mixture was stirred for 40 minutes, and 3-tert-butylaniline was added. The mixture was stirred for 1 hour, diluted with dichloromethane, washed twice each with sat. aq. NaHCO3 and 1.0 N aq. HCl, dried over MgSO4, and concentrated. Silica gel chromatography (0-2% MeOH:CH2Cl2) gave the title compound in 61% yield. MS (ES+) [M+H]+375.

Aufarbeitung

  1. stirringThe mixture was stirred for 1 hour
  2. washwashed twice each with sat. aq. NaHCO3 and 1.0 N aq. HCl
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-ed7a01bbd0af4d918e25666e97d4466e
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08450332B2

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