HCID 86727440, compound → HCID 86727439, compound

HRID 519071Notes

Reaction equation

HRID 519071 reaction equation
C([N:14]1[CH2:17][C:16]([CH3:47])([O:18][C:19]2[CH:20]=[C:21]3[C:30](=[CH:31][C:32]=2[C:33]([F:36])([F:35])[F:34])[O:29][CH2:28][C:27]2[N:22]3[CH:23]([CH3:46])[C:24](=[O:45])[N:25]([CH2:37][O:38][CH2:39][CH2:40][Si:41]([CH3:44])([CH3:43])[CH3:42])[N:26]=2)[CH2:15]1)(C1C=CC=CC=1)C1C=CC=CC=1>CCO.[OH-].[OH-].[Pd+2]>[CH3:46][CH:23]1[N:22]2[C:27]([CH2:28][O:29][C:30]3[C:21]2=[CH:20][C:19]([O:18][C:16]2([CH3:47])[CH2:15][NH:14][CH2:17]2)=[C:32]([C:33]([F:35])([F:34])[F:36])[CH:31]=3)=[N:26][N:25]([CH2:37][O:38][CH2:39][CH2:40][Si:41]([CH3:42])([CH3:44])[CH3:43])[C:24]1=[O:45]

Participants

4

Reactant 1

HCID 86727440HCID 86727440, compound

Product 1

HCID 86727439HCID 86727439, compoundYield 91.2%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of 6-(1-benzhydryl-3-methyl-azetidin-3-yloxy)-4-methyl-7-trifluoromethyl-2-(2-trimethylsilanyl-ethoxymethyl)-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one (0.031 g, 0.046 mmol) and Pd(OH)2/C (10%, 0.030 g) in EtOH (10 mL) was stirred at 50° C. under an atmosphere of H2 (50 psi) overnight. The reaction mixture was cooled to ambient temperature and filtered. The filtrate was evaporated in vacuo to give 4-methyl-6-(3-methyl-azetidin-3-yloxy)-7-trifluoromethyl-2-(2-trimethylsilanyl-ethoxymethyl)-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one (0.021 g crude) as an oil, which was used directly without purification. To a solution of 4-methyl-6-(3-methyl-azetidin-3-yloxy)-7-trifluoromethyl-2-(2-trimethylsilanyl-ethoxymethyl)-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one (0.021 g, 0.042 mmol) in DCM (3 mL) was added TFA (1 mL). The reaction was stirred at ambient temperature for 1.5 h then the solvent was removed in vacuo and the residue was diluted with dioxane (1 mL). Aqueous ammonium hydroxide (25%, 1 mL) was added and the reaction mixture was stirred at ambient temperature for 1.5 h. The solvent was removed in vacuo and the residue was purified by preparative HPLC (Table 3, Method 15) to give 4-methyl-6-(3-methyl-azetidin-3-yloxy)-7-trifluoromethyl-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one trifluoroacetic acid (0.0039 g, 25%). LC/MS (Table 1, Method 5) Rt=2.088 min; MS m/z: 371 [M+H]+.

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. filtrationfiltered
  3. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-c8a1a35fb5464f8aa1610890352dbbe6
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

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