Tetrabutylammonium Fluoride → HCID 57829753, compound

HRID 1855491Notes

Reaction equation

HRID 1855491 reaction equation
C([SiH2][O:6][C:7](C)(C)[C:8]1[CH:13]=[C:12]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][C:22]([F:25])([F:24])[F:23])=[CH:17][CH:16]=2)[N:11]=[C:10]([NH:26][C:27]2[CH:32]=[CH:31][C:30]([N:33]3[CH:37]=[C:36]([CH3:38])[N:35]=[CH:34]3)=[C:29]([O:39][CH3:40])[CH:28]=2)[CH:9]=1)(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH3:40][O:39][C:29]1[CH:28]=[C:27]([NH:26][C:10]2[CH:9]=[C:8]([CH2:7][OH:6])[CH:13]=[C:12]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][C:22]([F:24])([F:25])[F:23])=[CH:17][CH:16]=3)[N:11]=2)[CH:32]=[CH:31][C:30]=1[N:33]1[CH:37]=[C:36]([CH3:38])[N:35]=[CH:34]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 131732518HCID 131732518, compound

Product 1

HCID 57829753HCID 57829753, compoundYield 12.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

4-(tert-Butyl-dimethyl-silanyloxymethyl)-N-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-N′-(4-trifluoromethoxy-phenyl)-pyridine-2,6-diamine (50 mg, 0.083 mmol) was dissolved in 1 mL of tetrahydrofurane and tetrabutyl ammonium fluoride (44 mg, 0.17 mmol) were added. The mixture was stirred at 20° C. for 2 hours, concentrated in the rotatory evaporator and diluted with water. Extraction with ethyl acetate and purification by chromatography on amino-modified silica gel (Merck HPTLC Silica Gel 60 NH2F254S) using ethyl acetate/methanol (gradient 0 to 2% methanol) gave the pure title compound as a yellowish solid (5 mg, 10%). MS ISP (m/e): 486.2 (100) [(M+H)+]. 1H NMR (CDCl3, 300 MHz): δ (ppm)=7.58 (s, 1H), 7.41 (d, 2H), 7.19 (d, 1H), 7.20-7.05 (m, 3H), 6.97 (dxd, 1H), 6.83 (s, 1H), 6.78 (s broad, 1H), 6.67 (s broad, 1H), 6.40 (s, 1H), 6.33 (s, 1H), 4.59 (s, 2H), 3.67 (s, 3H), 2.28 (s, 3H).

Workup

  1. concentrationconcentrated in the rotatory evaporator
  2. additiondiluted with water
  3. extractionExtraction
  4. customwith ethyl acetate and purification by chromatography on amino-modified silica gel (Merck HPTLC Silica Gel 60 NH2F254S)

Sources & evidence

ORD record
ord-d23436a5556043468c60c38929c6b39c
Source dataset
uspto-grants-2015_02
Patent number
US08962834B2

Reaction notes

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