Acetyl chloride → 2-Chloro-7-(piperazin-1-yl)-1,5-naphthyridine

HRID 2199898Notes

Reaction equation

C(Cl)(=O)C.[Cl:5][C:6]1[N:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]=[CH:11][C:10]([N:16]1[CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18][CH2:17]1)=[CH:9]2>CO>[Cl:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][C:10]([N:16]3[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)=[CH:11][N:12]=2)[N:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Acetyl chloride (4.3 mL, 60.5 mmol) was added to MeOH (11 mL) at 0° C., the resulting solution was stirred at 0° C. for 30 min. To this solution, tert-butyl 4-(6-chloro-1,5-naphthyridin-3-yl)piperazine-1-carboxylate (D-18) (207 mg, 0.59 mmol, 1.0 eq) was added, and the mixture was stirred at RT for 2 h. The reaction was complete based on TLC analysis. The mixture was concentrated in vacuo to afford the desired product 2-chloro-7-(piperazin-1-yl)-1,5-naphthyridine (D-19), which was used for next reaction without further purification. 1H NMR (300 MHz, DMSO-d6) δ: 8.99 (d, J=2.7 Hz, 1H), 8.28 (d, J=8.7 Hz, 1H), 7.59 (d, J=2.7 Hz, 1H), 7.52 (d, J=8.7 Hz, 1H), 3.68 (m, 4H), 3.22 (m, 4H); ESI-MS m/z: 249.06[M+H]+.

Workup

stirringthe mixture was stirred at RT for 2 h
concentrationThe mixture was concentrated in vacuo

Sources & evidence

ORD record: ord-30a15ef5e0cc4743a92c0a1bd5c6d338
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09359352B2

Reaction notes

Loading…