Trifluoroacetic acid → Benzamide, 4-amino-N-cyclopropyl-

HRID 1943398Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1943398
[CH:1]1([NH:4][C:5]([C:7]2[CH:12]=[CH:11][C:10]([NH:13]C(=O)OC(C)(C)C)=[CH:9][CH:8]=2)=[O:6])[CH2:3][CH2:2]1.C(O)(C(F)(F)F)=O>>[NH2:13][C:10]1[CH:11]=[CH:12][C:7]([C:5]([NH:4][CH:1]2[CH2:2][CH2:3]2)=[O:6])=[CH:8][CH:9]=1

Komponenten

3

Edukt 2

HCID 6422Trifluoroacetic acidHCID 9210177HCID 9210177, Verbindung

Produkt 1

HCID 38082Benzamide, 4-amino-N-cyclopropyl-Ausbeute 101 %

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To a vial was added tert-butyl 4-(cyclopropylcarbamoyl)phenylcarbamate (326 mg, 1.18 mmol) and TFA (2 mL). The solution was stirred at 25° C. for 1 hour. The solution was concentrated in vacuo to give the crude product mixture which was purified by passing through a SCX column (2 g), eluting with the 2N ammonia in methanol to yield the pure product 4-amino-N-cyclopropylbenzamide (210 mg, 100%). LC/MS, m/z 177.05 (M+1). HPLC Rt, 0.63 min. Waters Sunfire C18 column (4.6×50 mm) 0%-100% B. Solvent B: (90% MeOH, 10% H2O, 0.1% TFA). Solvent A: (10% MeOH, 90% H2O, 0.1% TFA). Gradient, start % B=0, final % B=100, gradient time 4 min, hold at 100% B 1 min, flow rate 4 mL/min.

Aufarbeitung

  1. concentrationThe solution was concentrated in vacuo
  2. customto give the crude product mixture which
  3. customwas purified
  4. washeluting with the 2N ammonia in methanol

Quellen und Nachweise

ORD-Eintrag
ord-bb4401b19ace4c4b96dc5cc59ddd0c71
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08389527B2

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