Acetyl chloride → HCID 16040367, Verbindung

HRID 273517Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 273517
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][C:4]=1[C:10]1[CH:34]=[C:33]([CH3:35])[C:13]2[N:14]=[C:15]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][N:28]4[CH2:32][CH2:31][CH2:30][CH2:29]4)=[CH:21][CH:20]=3)[N:16]=[N:17][C:12]=2[CH:11]=1.CCN(CC)CC.[C:43](Cl)(=[O:45])[CH3:44]>C(Cl)Cl>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][C:43](=[O:45])[CH3:44])=[CH:5][C:4]=1[C:10]1[CH:34]=[C:33]([CH3:35])[C:13]2[N:14]=[C:15]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][N:28]4[CH2:32][CH2:31][CH2:30][CH2:29]4)=[CH:21][CH:20]=3)[N:16]=[N:17][C:12]=2[CH:11]=1

Komponenten

5

Edukt 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 248235674-Chloro-3-(5-methyl-3-{4-[2-(pyrrolidin-1-yl)ethoxy]anilino}-1,2,4-benzotriazin-7-yl)phenol--hydrogen chloride (1/1)

Produkt 1

HCID 16040367HCID 16040367, VerbindungAusbeute 80,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 4-chloro-3-{5-methyl-3-[4-(2-pyrrolidin-1-yl-ethoxy)-phenylamino]-benzo[1,2,4]triazin-7-yl}-phenol hydrochloride (1.0 equiv., 0.978 mmol) in DCM (30 mL) was added neat Et3N (10 equiv., 4.89 mmol) under an argon rich atmosphere and stirred for 10 minutes. Neat Acetyl chloride (1.2 equiv., 1.17 mmol) was added dropwise via syringe to the reaction mixture and allowed to stir at room temperature for 24 h. The reaction was quenched using saturated NaHCO3; the organics were dried over Na2SO4 and then concentrated down under reduced pressure. The resulting crude solid was then brought up in DCM and purified by flash chromatography using a solvent system of 85:10:5 (v/v/v) DCM/MeOH/Et3N. The fractions were concentrated under reduced pressure and precipitated out using 1:5 (v/v) DCM/hexanes to afford an orange solid (409.1 mg, 75% yield). 1H NMR (DMSO-d6): δ 1.68 (m, 4H), 2.29 (s, 3H), 2.51 (m, 4H), 2.63 (s, 3H), 2.78 (t, J=5.94 Hz, 2H), 4.07 (t, J=5.99 Hz, 2H), 6.99 (dd, J=7.05 Hz, 12.55 Hz, 2H), 7.27 (dd, J=5.90 Hz, 8.75 Hz, 1H), 7.41 (d, J=2.80 Hz, 1H), 7.67 (d, J=8.75 Hz, 1H), 7.85 (m, 1H), 7.93 (d, J=9.05 Hz, 2H), 8.17 (m, 1H), 10.83 (s, 1H). Rf=0.29 MS (ES+) m/z 520, LC retention time 2.57 minutes.

Aufarbeitung

  1. stirringto stir at room temperature for 24 h
  2. customThe reaction was quenched
  3. dry with materialthe organics were dried over Na2SO4
  4. concentrationconcentrated down under reduced pressure
  5. custompurified by flash chromatography
  6. concentrationThe fractions were concentrated under reduced pressure
  7. customprecipitated out

Quellen und Nachweise

ORD-Eintrag
ord-fd3ea97043ca4a5aa7d2b60cb9739d9d
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07456176B2

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