(1S,4S)-2-oxa-5-azabicyclo(2.2.1)heptane hydrochloride → HCID 72710206, compound

HRID 633728Notes

Reaction equation

HRID 633728 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10](=[O:28])[CH2:11][N:12]3[C:17]4=[N:18][C:19](Cl)=[CH:20][C:21](=[O:22])[N:16]4[CH2:15][CH2:14][C@H:13]3[C:24]([F:27])([F:26])[F:25])=[CH:9][C:4]=2[N:3]=[N:2]1.Cl.[C@H:30]12[CH2:36][C@H:33]([NH:34][CH2:35]1)[CH2:32][O:31]2>>[S:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10](=[O:28])[CH2:11][N:12]3[C:17]4=[N:18][C:19]([N:34]5[CH2:35][C@@H:30]6[CH2:36][C@H:33]5[CH2:32][O:31]6)=[CH:20][C:21](=[O:22])[N:16]4[CH2:15][CH2:14][C@H:13]3[C:24]([F:27])([F:26])[F:25])=[CH:9][C:4]=2[N:3]=[N:2]1

Participants

3

Reactant 2

HCID 21303398(1S,4S)-2-oxa-5-azabicyclo(2.2.1)heptane hydrochlorideHCID 118194497HCID 118194497, compound

Product 1

HCID 72710206HCID 72710206, compound

Procedure

210 mg (0.49 mmol) of (8S)-9-(2-benzo[1,2,3]thiadiazol-5-yl-2-oxoethyl)-2-chloro-8-trifluoromethyl-6,7,8,9-tetrahydropyrimido[1,2-a]pyrimidin-4-one and 79.50 mg (0.58 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), 100 mg of (8S)-9-(2-benzo[1,2,3]thiadiazol-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 are obtained, the characteristics of which are as follows:

Workup

  1. customAfter purification by chromatography on silica gel (eluent: 60/40 DCM/MeOH), 100 mg of (8S)-9-(2-benzo[1,2,3]thiadiazol-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
  2. customare obtained

Sources & evidence

ORD record
ord-b8174e71d92d4c049a77d5aac6167328
Source dataset
uspto-grants-2016_04
Patent number
US09321790B2

Reaction notes

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