Tetrabutylammonium Fluoride → HCID 67500397, compound

HRID 1484751Notes

Reaction equation

HRID 1484751 reaction equation
[Si]([O:8][CH2:9][CH2:10][N:11]([C:19]1[C:20]([Cl:30])=[N:21][N:22]([C:24]2[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=2)[CH:23]=1)[C:12](=[O:18])[CH:13]([CH3:17])[CH2:14][S:15][CH3:16])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.[Cl-].[Na+].O>[Cl:30][C:20]1[C:19]([N:11]([CH2:10][CH2:9][OH:8])[C:12](=[O:18])[CH:13]([CH3:17])[CH2:14][S:15][CH3:16])=[CH:23][N:22]([C:24]2[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=2)[N:21]=1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 67499417HCID 67499417, compound

Product 1

HCID 67500397HCID 67500397, compoundYield 56.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of N-(2-((tert-butyldimethylsilyl)oxy)ethyl)-N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-2-methyl-3-(methylthio)propanamide (0.180 g, 0.384 mmol) in tetrahydrofuran (1.54 ml) was added tetrabutylammonium fluoride (0.201 g, 0.767 mmol) and the reaction was stirred at room temperature for 2 hours. Brine was added and the mixture was extracted with ethyl acetate. The combined organic phases were concentrated and chromatographed (0-100% water/acetonitrile) to give N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-N-(2-hydroxyethyl)-2-methyl-3-(methylthio)propanamide as a white oil (0.081 g, 0.217 mmol, 56.5%): IR (thin film) 3423, 1654 cm−1; 1H NMR (400 MHz, CDCl3) δ 9.00 (d, J=2.5 Hz, 1H), 8.62 (dd, J=4.7, 1.2 Hz, 1H), 8.25 (s, 1H), 8.07 (ddd, J=8.3, 2.4, 1.3 Hz, 1H), 7.47 (dd, J=8.3, 4.7 Hz, 1H), 4.47-3.70 (m, 3H), 3.65-3.09 (m, 2H), 2.91-2.68 (m, 2H), 2.48 (dd, J=12.4, 5.0 Hz, 1H), 2.01 (s, 3H), 1.18 (d, J=6.5 Hz, 3H); ESIMS m/z 356 ([M+H]+).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. concentrationThe combined organic phases were concentrated
  3. customchromatographed (0-100% water/acetonitrile)

Sources & evidence

ORD record
ord-6b49f5c5e50d4ecf98979247fdd36deb
Source dataset
uspto-grants-2016_08
Patent number
US09422278B2

Reaction notes

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