Tetrabutylammonium Fluoride → HCID 178434035, compound

HRID 575078Notes

Reaction equation

HRID 575078 reaction equation
C([Si](C)(C)[O:6][CH2:7][C:8]([CH3:34])([C:28]1[NH:32][C:31]([CH3:33])=[N:30][N:29]=1)[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:6][CH2:7][C:8]([CH3:34])([C:28]1[NH:32][C:31]([CH3:33])=[N:30][N:29]=1)[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 178434036HCID 178434036, compound

Product 1

HCID 178434035HCID 178434035, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

9-[4-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-3-(5-methyl-4H-[1,2,4]triazol-3-yl)-but-1-ynyl]-4,5-dihydro-6-oxa-1,3a-diaza-benzo[e]azulene-2-carboxylic acid amide (120 mg, 0.2 mmol) was dissolved in THF (10 mL), TBAF (62.9 mg, 0.24 mmol) was added. The mixture was stirred at room temperature for 14 h. The mixture was purified via HPLC separation (0.1% HCOOH) to afford the titled compound (17.6 mg, 23.0%). 1H-NMR (DMSO-d6, 400 MHz): δ 114 (s, 1H), 8.45 (s, 1H), 7.77 (s, 1H), 7.51 (s, 1H), 7.29 (s, 1H), 7.11 (s, 1H), 6.98 (d, J=8.4 Hz, 1H), 5.05 (s, 1H), 4.45 (s, 4H), 3.77 (s, 2H), 2.29 (s, 3H), 1.21 (s, 3H). LCMS: [M+H]+=393.0.

Workup

  1. customThe mixture was purified via HPLC separation (0.1% HCOOH)

Sources & evidence

ORD record
ord-b3758ad3cdcc42aca24c3cd81903aced
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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