Water → HCID 178458504, compound

HRID 1025600Notes

Reaction equation

HRID 1025600 reaction equation
[OH:1][C:2]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[N:16](COCC[Si](C)(C)C)[N:15]=[CH:14][C:13]=2[C:25]#[N:26])=[CH:7][CH:6]=1)([CH3:4])[CH3:3].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>C(OCC)C>[OH:1][C:2]([C:5]1[CH:6]=[CH:7][C:8]([NH:11][C:12]2[C:13]([C:25]#[N:26])=[CH:14][NH:15][N:16]=2)=[CH:9][CH:10]=1)([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 71008367HCID 71008367, compound

Product 1

HCID 178458504HCID 178458504, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
110 °C

Procedure

5-(4-(2-Hydroxypropan-2-yl)phenylamino)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazole-4-carbonitrile (480 mg, 1.13 mmol) was taken up in a solution of tetrabutylammonium fluoride (1M, 16.8 ml) and the flask was sealed. The mixture was placed in an oil bath heated to 110° C. and stirred for 28 hours. The mixture was cooled to ambient. Water (60 ml) and diethyl ether (60 ml) were added and the material was shaken in a reparatory funnel and the organic phase was collected. The aqueous phase was back extracted with diethyl ether (2×50 ml). The organic phase was combined, dried from magnesium sulfate, filtered and stripped. The crude remainder was purified through Analogix flash column chromatography using ethyl acetate in hexanes (30% to 90% gradient, 40 g silica gel) to provide 3-(4-(2-hydroxypropan-2-yl)phenylamino)-1H-pyrazol-4-carbonitrile as an off-white powder (128 mg, 47% yield). LC/MS calc'd for C13H14N4O (m/e) 242.28, obs'd 241 (M−H, ES−).

Workup

  1. customthe flask was sealed
  2. customThe mixture was placed in an oil bath
  3. temperatureThe mixture was cooled to ambient
  4. stirringthe material was shaken in a reparatory funnel
  5. customthe organic phase was collected
  6. extractionThe aqueous phase was back extracted with diethyl ether (2×50 ml)
  7. dry with materialdried from magnesium sulfate
  8. filtrationfiltered
  9. customThe crude remainder was purified through Analogix flash column chromatography

Sources & evidence

ORD record
ord-e719fffafb95485ab712eb9aac2999be
Source dataset
uspto-grants-2014_05
Patent number
US08729078B2

Reaction notes

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