Trifluoroacetic acid → HCID 68487554, Verbindung

HRID 1875181Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1875181
CC([N:5]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([O:17][C:18]2[CH:23]=[C:22]([CH:24]3[CH2:26][CH2:25]3)[CH:21]=[C:20]([C:27]#[N:28])[CH:19]=2)[C:11]=1[F:29])C(=O)[O-])(C)C.C(O)(C(F)(F)F)=O.C(=O)(O)[O-].[Na+]>C(Cl)Cl.CCOC(C)=O>[NH2:5][CH2:9][C:10]1[C:11]([F:29])=[C:12]([O:17][C:18]2[CH:19]=[C:20]([CH:21]=[C:22]([CH:24]3[CH2:25][CH2:26]3)[CH:23]=2)[C:27]#[N:28])[C:13]([Cl:16])=[CH:14][CH:15]=1

Komponenten

6

Edukt 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 86761654HCID 86761654, Verbindung

Produkt 1

HCID 68487554HCID 68487554, VerbindungAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 1,1-dimethylethyl({4-chloro-3-[(3-cyano-5-cyclopropylphenyl)oxy]-2-fluorophenyl}methyl)carbamate (880 mg, 2.111 mmol) dissolved in DCM (15 ml) was added TFA (5.0 ml) and the reaction mixture was stirred for 30 minutes at RT. The reaction mixture was neutralized with saturated sodium bicarbonate, diluted with EtOAc, and the organics layer was separated. The solvent was evaporated and the crude material was purifed via silica gel chromatography to give 3-{[3-(aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-cyclopropylbenzonitrile (594 mg, 1.875 mmol, 89% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.38-7.52 (m, 2H), 7.22 (s, 1H), 7.04 (d, 2H), 3.73 (s, 2H), 1.91-2.01 (m, 1H), 1.89 (br. s., 2H), 0.89-1.04 (m, 2H), 0.64-0.81 (m, 2H).

Aufarbeitung

  1. customthe organics layer was separated
  2. customThe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-05aeee70b58041aebe21529220920975
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08304419B2

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