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Diisopropylethylamine → 4-[4-(7-Bromo-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino)-3-methoxy-phenyl]-piperidine-1-carboxylic acid tert-butyl ester

HRID 1262117
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1262117
[Br:1][C:2]1[N:10]2[C:5]([CH:6]=[N:7][C:8](O)=[N:9]2)=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.[N-](S(C(F)(F)F)(=O)=O)S(C(F)(F)F)(=O)=O.[C:36]([O:40][C:41]([N:43]1[CH2:48][CH2:47][CH:46]([C:49]2[CH:54]=[CH:53][C:52]([NH2:55])=[C:51]([O:56][CH3:57])[CH:50]=2)[CH2:45][CH2:44]1)=[O:42])([CH3:39])([CH3:38])[CH3:37]>CN(C=O)C.[Cl-].[Na+].O.O>[C:36]([O:40][C:41]([N:43]1[CH2:44][CH2:45][CH:46]([C:49]2[CH:54]=[CH:53][C:52]([NH:55][C:8]3[N:7]=[CH:6][C:5]4=[CH:4][CH:3]=[C:2]([Br:1])[N:10]4[N:9]=3)=[C:51]([O:56][CH3:57])[CH:50]=2)[CH2:47][CH2:48]1)=[O:42])([CH3:39])([CH3:38])[CH3:37]
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Komponenten

8

Edukt 4

HCID 81531DiisopropylethylamineHCID 4176748N-Propyl-Methyl Piperidinium Bis(trifluoroMethylsulfonyl)ImideHCID 57416157Tert-butyl 4-(4-amino-3-methoxyphenyl)piperidine-1-carboxylateHCID 178517419HCID 178517419, Verbindung

Produkt 1

HCID 667116754-[4-(7-Bromo-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino)-3-methoxy-phenyl]-piperidine-1-carboxylic acid tert-butyl ester
Ausbeute 52 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

In a 10 mL sealed tube, to 7-Bromo-pyrrolo[2,1-f][1,2,4]triazin-2-ol (150.0 mg, 0.701 mmol) and N,N-Diisopropylethylamine (0.488 mL, 2.80 mmol) in 3.8 mL of anhydrous DMF was added N-Phenylbis(trifluoromethanesulfonimide (263 mg, 0.736 mmol). After stirring at room temperature for 2 hours, 4-(4-Amino-3-methoxy-phenyl)-piperidin-1-carboxylic acid tert-butyl ester (214.7 mg, 0.701 mmol) was added. The reaction mixture was heated at 65° C. for 4 hours. The reaction was conc. in vacuo. Water and brine were added and the contents were extracted with DCM. The combined organic layers were dried with sodium sulfate, filtered, and conc. in vacuo. The reaction mixture was purified via silica gel column chromatography using 100:1 DCM:MeOH as the eluant to afford a the title compound as a red oil (52%). 1H NMR (DMSO-d6)-8.89 (s, 1H), 8.23 (d, 1H, J=8.20 Hz), 7.83 (s, 1H), 6.98-6.95 (m, 2H), 6.91 (d, 1H, J=4.72 Hz), 6.85 (d, 1H, J=8.52 Hz), 4.66-4.55 (br s, 1H), 4.16-3.99 (m, 3H), 3.89 (s, 3H), 2.87-2.75 (m, 2H), 1.78 (d, 2H, J=12.93 Hz), 1.70 (d, 1H, J=12.57 Hz), 1.42 (s, 9H).

Aufarbeitung

  1. customIn a 10 mL sealed tube
  2. temperatureThe reaction mixture was heated at 65° C. for 4 hours
  3. extractionthe contents were extracted with DCM
  4. dry with materialThe combined organic layers were dried with sodium sulfate
  5. filtrationfiltered
  6. customThe reaction mixture was purified via silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-c1ca8e1bc4c4455ebde5b81242c927a4
Quelldatensatz
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08471005B2

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