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p-Toluenesulfonic acid monohydrate → HCID 67980582, Verbindung

HRID 2173804
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2173804
[CH3:1][CH:2]([CH3:16])[CH2:3][C:4]([C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][N:7]=1)=O.[F:17][C:18]([F:33])([F:32])[C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][C:28]([NH2:31])=[CH:27][CH:26]=2)=[CH:21][CH:20]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C([BH3-])#N.[Na+]>COCCOC.CO.C(O)(=O)C>[CH3:1][CH:2]([CH3:16])[CH2:3][CH:4]([C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][N:7]=1)[NH:31][C:28]1[CH:29]=[CH:30][C:25]([C:22]2[CH:23]=[CH:24][C:19]([C:18]([F:17])([F:32])[F:33])=[CH:20][CH:21]=2)=[CH:26][CH:27]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 521998p-Toluenesulfonic acid monohydrateHCID 27827094'-(Trifluoromethyl)[1,1'-biphenyl]-4-amineHCID 5003444Sodium cyanoborohydrideHCID 67980853HCID 67980853, Verbindung

Produkt 1

HCID 67980582HCID 67980582, VerbindungAusbeute 15,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176
Acetic Acid
Lösungsmittel
HCID 887MethanolLösungsmittel
HCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

A solution of methyl 6-(3-methylbutanoyl)nicotinate (90 mg, 0.41 mmol), 4′-(trifluoromethyl)biphenyl-4-amine (145 mg, 0.610 mmol) and p-toluenesulfonic acid monohydrate (1.5 mg, 0.008 mmol) in anhydrous 1,2-dimethoxyethane (2.5 mL) was heated to 120° C. for 5 hours over activated molecular sieves in a sealed tube. The suspension was cooled to room temperature. Sodium cyanoborohydride (12.8 mg, 0.203 mmol) in methanol (1 mL) was added dropwise, immediately followed by acetic acid (0.1 mL). The resulting mixture was stirred overnight at room temperature. The reaction was concentrated and the crude residue was partitioned between ethyl acetate and saturated sodium bicarbonate. The aqueous layer was extracted again with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered and concentrated. Purification by preparative TLC (5:1 petroleum ether:ethyl acetate) gave methyl 6-(3-methyl-1-(4′-(trifluoromethyl) biphenyl-4-ylamino)butyl)nicotinate (28 mg, 15%) as a yellow solid. 1H NMR (400 MHz, CDCl3, δ): 9.19 (s, 1H), 8.21-8.24 (d, 1H), 7.54-7.60 (m, 4H), 7.43-7.45 (d, 1H), 7.35-7.37 (d, 2H), 6.61-6.63 (d, 2H), 4.65 (s, 1H), 3.93 (s, 3H), 1.74-1.75 (d, 2H), 0.92-1.02 (m, 6H).

Aufarbeitung

  1. concentrationThe reaction was concentrated
  2. customthe crude residue was partitioned between ethyl acetate and saturated sodium bicarbonate
  3. extractionThe aqueous layer was extracted again with ethyl acetate
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by preparative TLC (5:1 petroleum ether:ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-ffc2ca862cd24ecda672fd89ee6e4868
Quelldatensatz
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09056834B2

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