Triethylamine → HCID 178432421, compound

HRID 2268747Notes

Reaction equation

[Cl:1][C:2]1[S:10][C:9]2[S:8](=[O:12])(=[O:11])[N:7]=[C:6](F)[NH:5][C:4]=2[CH:3]=1.Cl.[CH3:15][C:16]1([NH2:20])[CH2:19][CH2:18][CH2:17]1.C(N(CC)CC)C>C(O)C>[Cl:1][C:2]1[S:10][C:9]2[S:8](=[O:12])(=[O:11])[N:7]=[C:6]([NH:20][C:16]3([CH3:15])[CH2:19][CH2:18][CH2:17]3)[NH:5][C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 6-chloro-3-fluoro-4H-thieno[3,2-e]-1,2,4-thiadiazine 1,1-dioxide (1.3 g, 5.3 mmol), 1-methylcyclobutylamine hydrochloride (1.0 g, 8.1 mmol) and triethylamine (2.5 ml, 18.1 mmol) in ethanol (10 ml) was stirred for 16 h at 50° C. and then for 5 h at 70° C. in a sealed flask. The cooled mixture was concentrated in vacuo and the residue was triturated with water (25 ml) followed by adjustment to pH <2 with 1M hydrochloric acid. The crude product was isolated by filtration, recrystallised from acetic acid and finally purified by chromatography (C18; 20-60% acetonitrile+0.01% TFA) to give 363 mg (22%) of the title compound; mp 294-296° C.; 1H-NMR (DMSO-d6): δ1.48 (s, 3H), 1.75-1.88 (m, 2H), 1.94-2.05 (m, 2H), 2.18-2.31 (m, 2H), 7.08 (s, 1H) 7.33 (br s, 1H), 10.67 (br s, 1H); LC-MS: m/e 306/308 (M+1)+.

Workup

waitfor 5 h at 70° C. in a sealed flask
concentrationThe cooled mixture was concentrated in vacuo
customthe residue was triturated with water (25 ml)
customThe crude product was isolated by filtration
customrecrystallised from acetic acid
customfinally purified by chromatography (C18; 20-60% acetonitrile+0.01% TFA)

Sources & evidence

ORD record: ord-93167e7bbb034244ba16c22f93076eda
Source dataset: uspto-grants-2001_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06329367B1

Reaction notes

Loading…