(1S,4S)-2-oxa-5-azabicyclo(2.2.1)heptane hydrochloride → (8S)-9-[2-(3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-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

HRID 633726Notes

Reaction equation

HRID 633726 reaction equation
Cl[C:2]1[N:3]=[C:4]2[N:12]([CH2:13][C:14]([C:16]3[CH:25]=[N:24][C:23]4[NH:22][CH2:21][CH2:20][O:19][C:18]=4[CH:17]=3)=[O:15])[C@H:11]([C:26]([F:29])([F:28])[F:27])[CH2:10][CH2:9][N:5]2[C:6](=[O:8])[CH:7]=1.Cl.[C@H:31]12[CH2:37][C@H:34]([NH:35][CH2:36]1)[CH2:33][O:32]2>>[O:19]1[CH2:20][CH2:21][NH:22][C:23]2[N:24]=[CH:25][C:16]([C:14](=[O:15])[CH2:13][N:12]3[C:4]4=[N:3][C:2]([N:35]5[CH2:36][C@@H:31]6[CH2:37][C@H:34]5[CH2:33][O:32]6)=[CH:7][C:6](=[O:8])[N:5]4[CH2:9][CH2:10][C@H:11]3[C:26]([F:28])([F:27])[F:29])=[CH:17][C:18]1=2

Participants

3

Reactant 2

HCID 21303398(1S,4S)-2-oxa-5-azabicyclo(2.2.1)heptane hydrochlorideHCID 118194446(8S)-2-chloro-9-[2-(3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-yl)-2-oxoethyl]-8-trifluoromethyl-6,7,8,9-tetrahydropyrimido[1,2-a]pyrimidin-4-one

Product 1

HCID 118194480(8S)-9-[2-(3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-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

Procedure

110 mg (0.25 mmol) of (8S)-2-chloro-9-[2-(3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-yl)-2-oxoethyl]-8-trifluoromethyl-6,7,8,9-tetrahydropyrimido[1,2-a]pyrimidin-4-one and 41.64 mg (0.31 mmol) of (1S,4S)-2-oxa-5-azabicyclo[2.2.1]heptane hydrochloride were used in the reaction. After purification by passing through an RP18 reverse-phase column (eluent: from 100% H2O to 100% CH3CN over 30 minutes), 30 mg of (8S)-9-[2-(3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-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
  2. customby passing through an RP18 reverse-phase column (eluent: from 100% H2O to 100% CH3CN over 30 minutes), 30 mg of (8S)-9-[2-(3,4-dihydro-2H-pyrido[3,2-b][1,4]oxazin-7-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
  3. customare obtained

Sources & evidence

ORD record
ord-67e5df993f3041eba6242e437c108597
Source dataset
uspto-grants-2016_04
Patent number
US09321790B2

Reaction notes

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