Hydrochloric Acid → (6-(1,4-Diazepan-1-yl)pyridin-2-yl)(2-amino-5-bromopyridin-3-yl)methanone

HRID 401494Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 401494
[NH2:1][C:2]1[N:29]=[CH:28][C:27]([Br:30])=[CH:26][C:3]=1[C:4]([C:6]1[N:11]=[C:10]([N:12]2[CH2:18][CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][CH2:13]2)[CH:9]=[CH:8][CH:7]=1)=[O:5].Cl>O1CCOCC1>[N:12]1([C:10]2[N:11]=[C:6]([C:4]([C:3]3[C:2]([NH2:1])=[N:29][CH:28]=[C:27]([Br:30])[CH:26]=3)=[O:5])[CH:7]=[CH:8][CH:9]=2)[CH2:18][CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 57690601Tert-butyl 4-(6-(2-amino-5-bromonicotinoyl)pyridin-2-yl)-1,4-diazepane-1-carboxylate

Produkt 1

HCID 24871523(6-(1,4-Diazepan-1-yl)pyridin-2-yl)(2-amino-5-bromopyridin-3-yl)methanoneAusbeute 36 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel2×

Versuchsvorschrift

To a suspension of tert-butyl 4-(6-(2-amino-5-bromonicotinoyl)pyridin-2-yl)-1,4-diazepane-1-carboxylate (50 mg, 0.1 mmol) in 1,4-dioxane (2 ml) at 0° C. was added 4 M HCl in 1,4-dioxane (1 ml). The resulting mixture was stirred at room temperature for 5 hours. The reaction mixture was concentrated to dryness to leave an orange solid which was further purified by reverse phase preparative HPLC [Waters Sunfire C18, 10M, 100 Å column, gradient 10%-95% B (solvent A: 0.05% TFA in water; solvent B: CH3CN) over 16 minutes at 25 mL/min]. The fractions were collected, passed through a sodium bicarbonate cartridge and freeze-dried to give the title compound as a yellow solid (13.5 mg, 36% yield).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated to dryness
  2. customto leave an orange solid which
  3. customwas further purified by reverse phase preparative HPLC [Waters Sunfire C18, 10M, 100 Å column, gradient 10%-95% B (solvent A: 0.05% TFA in water; solvent B: CH3CN) over 16 minutes at 25 mL/min]
  4. customThe fractions were collected
  5. customfreeze-dried

Quellen und Nachweise

ORD-Eintrag
ord-6c7e86fc56b7493abbac5557ee20ec85
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08741931B2

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