Trifluoroacetic acid → HCID 86727441, compound

HRID 519072Notes

Reaction equation

HRID 519072 reaction equation
[CH3:1][CH:2]1[N:15]2[C:6]([CH2:7][O:8][C:9]3[C:14]2=[CH:13][C:12]([O:16][C:17]2([CH3:21])[CH2:20][NH:19][CH2:18]2)=[C:11]([C:22]([F:25])([F:24])[F:23])[CH:10]=3)=[N:5][N:4](COCC[Si](C)(C)C)[C:3]1=[O:34].[C:35]([OH:41])([C:37]([F:40])([F:39])[F:38])=[O:36]>C(Cl)Cl>[F:38][C:37]([F:40])([F:39])[C:35]([OH:41])=[O:36].[CH3:1][CH:2]1[N:15]2[C:6]([CH2:7][O:8][C:9]3[C:14]2=[CH:13][C:12]([O:16][C:17]2([CH3:21])[CH2:20][NH:19][CH2:18]2)=[C:11]([C:22]([F:24])([F:25])[F:23])[CH:10]=3)=[N:5][NH:4][C:3]1=[O:34]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86727439HCID 86727439, compound

Product 1

HCID 86727441HCID 86727441, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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. customwas used directly without purification
  2. customthe solvent was removed in vacuo
  3. additionthe residue was diluted with dioxane (1 mL)
  4. additionAqueous ammonium hydroxide (25%, 1 mL) was added
  5. stirringthe reaction mixture was stirred at ambient temperature for 1.5 h
  6. customThe solvent was removed in vacuo
  7. customthe residue was purified by preparative HPLC (Table 3, Method 15)

Sources & evidence

ORD record
ord-c44187001a834d4c902b7a067b630e9d
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

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