Triethylamine → HCID 72709878, compound

HRID 633745Notes

Reaction equation

Cl[C:2]1[N:3]=[C:4]2[N:12]([CH2:13][C:14](=[O:19])[C:15]([CH3:18])([CH3:17])[CH3:16])[C@H:11]([C:20]([F:23])([F:22])[F:21])[CH2:10][CH2:9][N:5]2[C:6](=[O:8])[CH:7]=1.Cl.[C@H:25]12[CH2:31][C@H:28]([NH:29][CH2:30]1)[CH2:27][O:26]2.C(N(CC)CC)C>>[CH3:16][C:15]([CH3:18])([CH3:17])[C:14](=[O:19])[CH2:13][N:12]1[C:4]2=[N:3][C:2]([N:29]3[CH2:30][C@@H:25]4[CH2:31][C@H:28]3[CH2:27][O:26]4)=[CH:7][C:6](=[O:8])[N:5]2[CH2:9][CH2:10][C@H:11]1[C:20]([F:23])([F:22])[F:21]

Participants

Reactant 3

HCID 8471Triethylamine

HCID 21303398(1S,4S)-2-oxa-5-azabicyclo(2.2.1)heptane hydrochloride

HCID 118194317HCID 118194317, compound

Product 1

HCID 72709878HCID 72709878, compound

Procedure

180 mg (0.511 mmol) of (8S)-2-chloro-9-(3,3-dimethyl-2-oxobutyl)-8-trifluoromethyl-6,7,8,9-tetrahydropyrimido[1,2-a]pyrimidin-4-one, 76.32 mg (0.563 mmol) of (1S,4S)-2-oxa-5-azabicyclo[2.2.1]heptane hydrochloride and 179 μl (1.28 mmol) of triethylamine were used in the reaction. After purification by chromatography on silica gel (eluent A/B: DCM/MeOH, gradient A/B: t 0 min 0% B, t 15 min 4% B, t 18 min 4% B, t 33 min 10% B), 130 mg of (8S)-9-(3,3-dimethyl-2-oxobutyl)-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 were obtained, corresponding to the following characteristics:

Workup

customAfter purification by chromatography on silica gel (eluent A/B: DCM/MeOH, gradient A/B: t 0 min 0% B, t 15 min 4% B, t 18 min 4% B, t 33 min 10% B), 130 mg of (8S)-9-(3,3-dimethyl-2-oxobutyl)-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
customwere obtained, corresponding to the following characteristics

Sources & evidence

ORD record: ord-e839fc9bf7994ed887f8b9e8645b4693
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321790B2

Reaction notes

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