Triethylamine → HCID 72710121, compound

HRID 633716Notes

Reaction equation

Cl[C:2]1[N:3]=[C:4]2[N:12]([CH2:13][C:14]([C:16]3[S:20][CH:19]=[N:18][C:17]=3[CH3:21])=[O:15])[C@H:11]([C:22]([F:25])([F:24])[F:23])[CH2:10][CH2:9][N:5]2[C:6](=[O:8])[CH:7]=1.Cl.[C@H:27]12[CH2:33][C@H:30]([NH:31][CH2:32]1)[CH2:29][O:28]2.C(N(CC)CC)C>O>[CH3:21][C:17]1[N:18]=[CH:19][S:20][C:16]=1[C:14](=[O:15])[CH2:13][N:12]1[C:4]2=[N:3][C:2]([N:31]3[CH2:32][C@@H:27]4[CH2:33][C@H:30]3[CH2:29][O:28]4)=[CH:7][C:6](=[O:8])[N:5]2[CH2:9][CH2:10][C@H:11]1[C:22]([F:25])([F:24])[F:23]

Participants

Conditions

Temperature: 130 °C

Procedure

170 mg (0.511 mmol) of (8S)-2-chloro-9-[2-(4-methylthiazol-5-yl)-2-oxoethyl]-8-trifluoromethyl-6,7,8,9-tetrahydropyrimido[1,2-a]pyrimidin-4-one and 70.42 mg (0.52 mmol) of (1S,4S)-2-oxa-5-azabicyclo[2.2.1]heptane hydrochloride are mixed together. The powder obtained is placed in a tube and 151 μl (1.08 mmol) of triethylamine are added. The tube is sealed and heated at 130° C. in an oil bath for 3 hours. The crude product obtained is taken up in water and extracted with ethyl acetate. The organic phase is dried over magnesium sulfate and then evaporated to dryness. The residue is purified by chromatography on silica gel (eluent: 95/5 EtOAc/MeOH) to give 120 mg of (8S)-9-[2-(4-methylthiazol-5-yl)-2-oxoethyl]-2-(1S,4S)-2-oxa-5-azabicyclo[2.2.1]hept-5-yl-8-trifluoromethyl-6,7,8,9-tetrahydropyrimido[1,2-a]pyrimidin-4-one, the characteristics of which are as follows:

Workup

customThe powder obtained
customis placed in a tube
customThe tube is sealed
customThe crude product obtained
extractionextracted with ethyl acetate
dry with materialThe organic phase is dried over magnesium sulfate
customevaporated to dryness
customThe residue is purified by chromatography on silica gel (eluent: 95/5 EtOAc/MeOH)

Sources & evidence

ORD record: ord-70417c8c9c704dbbb7e55d1d04e5d091
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321790B2

Reaction notes

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