Dimethylformamide → 3-[3-(6-Amino-5-benzothiazol-2-ylpyridin-3-yl)-prop-2-ynyl]-1,1-dimethylurea

Reaktionsgleichung

[NH2:1][CH2:2][C:3]#[C:4][C:5]1[CH:6]=[C:7]([C:12]2[S:13][C:14]3[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=3[N:16]=2)[C:8]([NH2:11])=[N:9][CH:10]=1.[CH3:21][N:22]([CH3:26])[C:23](Cl)=[O:24].CN(C=O)C.CCN(C(C)C)C(C)C>>[NH2:11][C:8]1[N:9]=[CH:10][C:5]([C:4]#[C:3][CH2:2][NH:1][C:23](=[O:24])[N:22]([CH3:26])[CH3:21])=[CH:6][C:7]=1[C:12]1[S:13][C:14]2[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=2[N:16]=1

Komponenten

Edukt 4

HCID 6228Dimethylformamide

HCID 6598Dimethylcarbamoyl Chloride

HCID 81531Diisopropylethylamine

HCID 675208705-(3-Aminoprop-1-ynyl)-3-benzothiazol-2-ylpyridin-2-ylamine

Produkt 1

HCID 675209823-[3-(6-Amino-5-benzothiazol-2-ylpyridin-3-yl)-prop-2-ynyl]-1,1-dimethylurea

Versuchsvorschrift

A mixture of 5-(3-aminoprop-1-ynyl)-3-benzothiazol-2-ylpyridin-2-ylamine (10.0 mg, 0.0357 mmol), N,N-dimethylcarbamoyl chloride (3.60 uL, 0.0392 mmol), DMF (1 mL, 0.01 mol) and DIPEA (0.03 mL, 0.2 mmol) was stirred at rt for 30 min. The solution was used directly for HPLC purification. The fractions containing the pure product were concentrated in vacuo to afford the title compound as a yellow solid. 1H NMR (400 MHz, CD3OD): δ=2.93 (s, 6H), 4.13-4.18 (m, 2H), 7.39-7.45 (m, 1H), 7.51 (td, J=7.7, 1.3 Hz, 1H), 7.96 (d, J=7.3 Hz, 1H), 8.01 (d, J=8.1 Hz, 1H), 8.09 (d, J=2.0 Hz, 1H), 8.14 (s, 1H). MS (ES+): m/z=352.11 (100) [MH+]. HPLC: tR=3.11 min (ZQ3, polar—5 min).