(1S,4S)-2-oxa-5-azabicyclo(2.2.1)heptane hydrochloride → HCID 72710210, compound

HRID 633730Notes

Reaction equation

HRID 633730 reaction equation
Cl[C:2]1[N:3]=[C:4]2[N:12]([CH2:13][C:14]3[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[N:16]([CH3:23])[N:15]=3)[C@H:11]([C:24]([F:27])([F:26])[F:25])[CH2:10][CH2:9][N:5]2[C:6](=[O:8])[CH:7]=1.Cl.[C@H:29]12[CH2:35][C@H:32]([NH:33][CH2:34]1)[CH2:31][O:30]2>>[CH3:23][N:16]1[C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:14]([CH2:13][N:12]2[C:4]3=[N:3][C:2]([N:33]4[CH2:34][C@@H:29]5[CH2:35][C@H:32]4[CH2:31][O:30]5)=[CH:7][C:6](=[O:8])[N:5]3[CH2:9][CH2:10][C@H:11]2[C:24]([F:25])([F:27])[F:26])=[N:15]1

Participants

3

Reactant 2

HCID 21303398(1S,4S)-2-oxa-5-azabicyclo(2.2.1)heptane hydrochlorideHCID 118194302HCID 118194302, compound

Product 1

HCID 72710210HCID 72710210, compound

Procedure

250 mg (0.63 mmol) of (8S)-2-chloro-9-(1-methyl-1H-indazol-3-ylmethyl)-8-trifluoromethyl-6,7,8,9-tetrahydropyrimido[1,2-a]pyrimidin-4-one and 102.26 mg (0.75 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), 230 mg of (8S)-9-(1-methyl-1H-indazol-3-ylmethyl)-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), 230 mg of (8S)-9-(1-methyl-1H-indazol-3-ylmethyl)-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-002442a4fc0048378962b75f9b22849c
Source dataset
uspto-grants-2016_04
Patent number
US09321790B2

Reaction notes

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