(1S,4S)-2-oxa-5-azabicyclo(2.2.1)heptane hydrochloride → HCID 72709216, compound

HRID 633737Notes

Reaction equation

HRID 633737 reaction equation
Cl[C:2]1[N:3]=[C:4]2[N:12]([CH2:13][C:14]([C:16]3[N:17]([CH3:21])[N:18]=[CH:19][CH:20]=3)=[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>>[CH3:21][N:17]1[C:16]([C:14](=[O:15])[CH2:13][N:12]2[C:4]3=[N:3][C:2]([N:31]4[CH2:32][C@@H:27]5[CH2:33][C@H:30]4[CH2:29][O:28]5)=[CH:7][C:6](=[O:8])[N:5]3[CH2:9][CH2:10][C@H:11]2[C:22]([F:25])([F:24])[F:23])=[CH:20][CH:19]=[N:18]1

Participants

3

Reactant 2

HCID 21303398(1S,4S)-2-oxa-5-azabicyclo(2.2.1)heptane hydrochlorideHCID 118194427HCID 118194427, compound

Product 1

HCID 72709216HCID 72709216, compound

Procedure

230 mg (0.61 mmol) of (8S)-2-chloro-9-[2-(2-methyl-2H-pyrazol-3-yl)-2-oxoethyl]-8-trifluoromethyl-6,7,8,9-tetrahydropyrimido[1,2-a]pyrimidin-4-one and 107.90 mg (0.79 mmol) of (1S,4S)-2-oxa-5-azabicyclo[2.2.1]heptane hydrochloride were used in the reaction. After purification by chromatography on silica gel (eluent: 60/40 DCM/MeOH), 160 mg of (8S)-9-[2-(2-methyl-2H-pyrazol-3-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 are obtained, the characteristics of which are as follows:

Workup

  1. customAfter purification by chromatography on silica gel (eluent: 60/40 DCM/MeOH), 160 mg of (8S)-9-[2-(2-methyl-2H-pyrazol-3-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
  2. customare obtained

Sources & evidence

ORD record
ord-903ecb08edd8478b8479ac1671646552
Source dataset
uspto-grants-2016_04
Patent number
US09321790B2

Reaction notes

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