Tetrabutylammonium Fluoride → HCID 86727594, compound

HRID 519184Notes

Reaction equation

HRID 519184 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[C:16]3[C:25](=[CH:26][C:27]=2[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[F:34])[O:24][CH2:23][C:22]2[N:17]3[CH:18]([CH3:44])[C:19](=[O:43])[N:20](COCC[Si](C)(C)C)[N:21]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[C:16]3[C:25](=[CH:26][C:27]=2[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[F:34])[O:24][CH2:23][C:22]2[N:17]3[CH:18]([CH3:44])[C:19](=[O:43])[NH:20][N:21]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86727595HCID 86727595, compound

Product 1

HCID 86727594HCID 86727594, compoundYield 54.2%

Conditions

Temperature
80 °C

Procedure

4-[7-(2-Fluoro-phenyl)-4-methyl-3-oxo-2-(2-trimethylsilanyl-ethoxymethyl)-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-yl]-piperazine-1-carboxylic acid tert-butyl ester (0.2 g, 0.320 mmol) was dissolved in tetrabutylammonium fluoride (1M in THF, 20 mL, 20.00 mmol) and the reaction mixture was heated at 80° C. overnight. The reaction mixture was cooled to ambient temperature, quenched by the addition of water (20 mL) and extracted with EtOAc (3×15 mL). The combined organic phase was washed with brine (2×30 mL) and concentrated in vacuo. The residue was purified by column chromatography on silica gel (eluting with 7-50% EtOAc in petroleum ether) to give 4-[7-(2-fluoro-phenyl)-4-methyl-3-oxo-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-yl]-piperazine-1-carboxylic acid tert-butyl ester (0.086 g, 54%) as a colorless solid. 1H NMR (400 MHz, CDCl3) δ 8.07 (brs, 1H), 7.40 (m, 1H), 7.36-7.29 (m, 1H), 7.22-7.09 (m, 2H), 6.96 (s, 1H), 6.62 (s, 1H), 4.75 (q, J=6.8 Hz, 1H), 4.60 (d, J=13.2 Hz, 2H), 3.26 (brs, 4H), 2.72 (brs, 4H), 1.57 (s, 3H), 1.45 (s, 9H).

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. customquenched by the addition of water (20 mL)
  3. extractionextracted with EtOAc (3×15 mL)
  4. washThe combined organic phase was washed with brine (2×30 mL)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography on silica gel (eluting with 7-50% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-6f5c84c3eb4f4a90b41ea33defae243a
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

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