(S)-2-(2-Methoxyethyl)piperazine → HCID 10317297, compound

HRID 131446Notes

Reaction equation

[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:14]=[C:13](SC)[C:12]3[CH:11]=[C:10]([CH3:17])[S:9][C:8]=3[NH:7][C:6]=2[CH:18]=1.[CH3:19][O:20][CH2:21][CH2:22][C@H:23]1[CH2:28][NH:27][CH2:26][CH2:25][NH:24]1>C(O)(C)C>[NH4+:7].[OH-:20].[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:14]=[C:13]([N:27]3[CH2:26][CH2:25][NH:24][C@@H:23]([CH2:22][CH2:21][O:20][CH3:19])[CH2:28]3)[C:12]3[CH:11]=[C:10]([CH3:17])[S:9][C:8]=3[NH:7][C:6]=2[CH:18]=1

Participants

Conditions

Temperature: 81.5 °C

Procedure

Stir 6-fluoro-2-methyl-10-methylsulfanyl-4H-3-thia-4,9-diaza-benzo[f]azulene (3.40 g, 12.2 mmol) and (S)-2-(2-methoxy-ethyl)-piperazine (2.20 g, 15.3 mmol) in isopropyl alcohol (20 mL) at ambient temperature under nitrogen for 20-30 minutes to dissolve. Heat to reflux (80-83° C.) for 3-4 days, and then allow cooling to ambient temperature. Concentrate the mixture under reduced pressure to give a residue. Purify the residue by flash chromatography, eluting with 90:10:1→80:20:1/EtOAc:MeOH:c. NH4OH to give 4.06 g (89%) the title compound. 1H NMR (400 MHz, DMSO-d6) δ 7.75 (bs, 1H), 6.78 (m, 1H), 6.68 (m, 1H), 6.53 (m, 1H), 6.35 (s, 1H), 3.80 (m, 2H), 3.40 (m, 2H), 3.23 (s, 3H), 2.88 (m, 1H), 2.71 (m, 3H), 2.41 (m, 1H), 2.30 (bs, 1H), (s, 3H), 1.53 (m, 2H). HRMS (ES) exact mass M+H calcd for C19H23FN4OS 375.1655; found 375.1663.

Workup

dissolutionto dissolve
temperatureHeat
temperatureallow cooling to ambient temperature
concentrationConcentrate the mixture under reduced pressure
customto give a residue
customPurify the residue by flash chromatography
washeluting with 90:10:1→80:20:1/EtOAc

Sources & evidence

ORD record: ord-26b3793ff3274a8ebaa5c81a94ed9efe
Source dataset: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07384934B2

Reaction notes

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