Acetyl chloride → N-(3-(5-cyanopyrazin-2-ylamino)isoquinolin-8-yl)acetamide

HRID 40683

Reaktionsgleichung

Reaktionsgleichung von HRID 40683
[C:1](Cl)(=[O:3])[CH3:2].[NH2:5][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:15]=1[CH:14]=[N:13][C:12]([NH:16][C:17]1[N:18]=[CH:19][C:20]([C:23]#[N:24])=[N:21][CH:22]=1)=[CH:11]2.C(N(C(C)C)CC)(C)C>ClCCCl>[C:23]([C:20]1[N:21]=[CH:22][C:17]([NH:16][C:12]2[N:13]=[CH:14][C:15]3[C:10]([CH:11]=2)=[CH:9][CH:8]=[CH:7][C:6]=3[NH:5][C:1](=[O:3])[CH3:2])=[N:18][CH:19]=1)#[N:24]

Komponenten

5

Edukt 3

HCID 6367Acetyl chloride2×HCID 81531DiisopropylethylamineHCID 442045585-(8-Aminoisoquinolin-3-ylamino)pyrazine-2-carbonitrile

Produkt 1

HCID 44204559N-(3-(5-cyanopyrazin-2-ylamino)isoquinolin-8-yl)acetamideAusbeute 32 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

Acetyl chloride (13 mg, 0.16 mmol) was added to a solution of 5-(8-aminoisoquinolin-3-ylamino)pyrazine-2-carbonitrile (36 mg, 0.14 mmol) and diisopropylethylamine (39 mg, 0.30 mmol) in DCE (1.5 mL). The reaction mixture stirred at room temperature for 16 hours and another portion of acetyl chloride (6.5 mg, 0.08 mmol) was added. Stirring was continued for a further 24 hours. The reaction mixture was washed once with water and the organic phase was dried (Na2SO4) and concentrated to dryness. Preparative HPLC gave N-(3-(5-cyanopyrazin-2-ylamino)isoquinolin-8-yl)acetamide (13.4 mg, 0.044 mmol, 32%). 1H NMR (d6-DMSO, 400 MHz) δ 11.05 (br s, 1H), 10.20 (s, 1H), 9.36 (s, 1H), 8.82 (d, 1H, J=1.2 Hz), 8.72 (d, 1H, J=1.2 Hz), 8.48 (s, 1H), 7.65-7.75 (m, 3H), 2.22 (s, 3H). LC-MS (2) Rt=1.96 min; m/z (ESI+) 305 (M+H).

Aufarbeitung

  1. stirringStirring
  2. waitwas continued for a further 24 hours
  3. washThe reaction mixture was washed once with water
  4. dry with materialthe organic phase was dried (Na2SO4)
  5. concentrationconcentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-ac3b96b0049f4acba0cc8a0b36463c4e
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08530468B2

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