Triethylamine → HCID 72708974, compound

HRID 633702Notes

Reaction equation

HRID 633702 reaction equation
Cl[C:2]1[N:3]=[C:4]2[N:12]([CH2:13][C:14]([C:16]3[C:17]([CH3:22])=[N:18][O:19][C:20]=3[CH3:21])=[O:15])[C@H:11]([C:23]([F:26])([F:25])[F:24])[CH2:10][CH2:9][N:5]2[C:6](=[O:8])[CH:7]=1.Cl.[C@H:28]12[CH2:34][C@H:31]([NH:32][CH2:33]1)[CH2:30][O:29]2.C(N(CC)CC)C>O>[CH3:22][C:17]1[C:16]([C:14](=[O:15])[CH2:13][N:12]2[C:4]3=[N:3][C:2]([N:32]4[CH2:33][C@@H:28]5[CH2:34][C@H:31]4[CH2:30][O:29]5)=[CH:7][C:6](=[O:8])[N:5]3[CH2:9][CH2:10][C@H:11]2[C:23]([F:26])([F:25])[F:24])=[C:20]([CH3:21])[O:19][N:18]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21303398(1S,4S)-2-oxa-5-azabicyclo(2.2.1)heptane hydrochlorideHCID 118194484(8S)-2-chloro-9-[2-(3,5-dimethylisoxazol-4-yl)-2-oxoethyl]-8-trifluoromethyl-6,7,8,9-tetrahydropyrimido[1,2-a]pyrimidin-4-one

Product 1

HCID 72708974HCID 72708974, compoundYield 56.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

200 mg (0.51 mmol) of (8S)-2-chloro-9-[2-(3,5-dimethylisoxazol-4-yl)-2-oxoethyl]-8-trifluoromethyl-6,7,8,9-tetrahydropyrimido[1,2-a]pyrimidin-4-one and 83.28 mg (0.61 mmol) of (1S,4S)-2-oxa-5-azabicyclo[2.2.1]heptane hydrochloride are mixed together. The powder obtained is placed in a tube and 178 μl (1.28 mmol) of triethylamine are added. The tube is sealed and heated at 130° C. in an oil bath for 6 hours. The crude product obtained is taken up in water and extracted with ethyl acetate. The organic phase is dried over magnesium sulfate and then evaporated to dryness. The residue is purified by chromatography on silica gel (eluent: 95/5 EtOAc/MeOH) to give 130 mg of (8S)-9-[2-(3,5-dimethylisoxazol-4-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, the characteristics of which are as follows:

Workup

  1. customThe powder obtained
  2. customis placed in a tube
  3. customThe tube is sealed
  4. customThe crude product obtained
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organic phase is dried over magnesium sulfate
  7. customevaporated to dryness
  8. customThe residue is purified by chromatography on silica gel (eluent: 95/5 EtOAc/MeOH)

Sources & evidence

ORD record
ord-7877fa9d667747208e653b802e69923c
Source dataset
uspto-grants-2016_04
Patent number
US09321790B2

Reaction notes

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