Tetrabutylammonium Fluoride → HCID 71714724, compound

HRID 575071Notes

Reaction equation

HRID 575071 reaction equation
C([Si](C)(C)[O:6][CH2:7][C:8]([OH:29])([CH3:28])[C:9]#[C:10][C:11]1[CH:12]=[CH:13][C:14]2[O:23][CH2:22][CH2:21][N:20]3[C:16](=[N:17][C:18]([C:24]([NH2:26])=[O:25])=[CH:19]3)[C:15]=2[CH:27]=1)(C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[OH:29][C:8]([CH3:28])([CH2:7][OH:6])[C:9]#[C:10][C:11]1[CH:12]=[CH:13][C:14]2[O:23][CH2:22][CH2:21][N:20]3[C:16](=[N:17][C:18]([C:24]([NH2:26])=[O:25])=[CH:19]3)[C:15]=2[CH:27]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86693099HCID 86693099, compound

Product 1

HCID 71714724HCID 71714724, compoundYield 46.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of compound 9-[4-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-3-methyl-but-1-ynyl]-4,5-dihydro-6-oxa-1,3a-diaza-benzo[e]azulene-2-carboxylic acid amide (300 mg, 0.66 mmol) in THF (20 mL) was added TBAF (340 mg, 1.3 mmol) at 0° C. for about 1 h. After washed with water and extracted with EtOAc, the crude product was purified by Pre-HPLC to get the titled compound (100.0 mg, yield 46.5%). LCMS=328.1 [M+H]+; 1H NMR (DMSO-d6, 400 MHz) δ 8.50 (d, J=2.0 Hz, 1H), 7.84 (s, 1H), 7.64 (s, 1H), 7.34 (d, J=8.4 Hz, 1H), 7.26 (s, 1H), 7.04 (d, J=8.4 Hz, 1H), 4.50 (s, 4H), 3.45-3.37 (q, J=10.4 Hz, 2H), 1.39 (s, 3H).

Workup

  1. washAfter washed with water
  2. extractionextracted with EtOAc
  3. customthe crude product was purified by Pre-HPLC

Sources & evidence

ORD record
ord-c9187a75b50e47f49365cfb60588e4a0
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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