Tetrabutylammonium Fluoride → HCID 67085451, compound

HRID 1047458Notes

Reaction equation

HRID 1047458 reaction equation
C([Si](C1C=CC=CC=1)(C1C=CC=CC=1)[O:6][CH:7]1[CH2:11][CH:10]([N:12]2[CH:20]=[N:19][C:18]3[C:13]2=[N:14][C:15]([NH2:22])=[N:16][C:17]=3[Cl:21])[C:9](=[CH2:23])[CH:8]1[CH2:24][O:25][C:26]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.CO>[NH2:22][C:15]1[N:16]=[C:17]([Cl:21])[CH:18]2[CH:13]([N:14]=1)[N:12]([CH:10]1[CH2:11][CH:7]([OH:6])[CH:8]([CH2:24][O:25][C:26]([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:9]1=[CH2:23])[CH:20]=[N:19]2

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 76035569HCID 76035569, compound

Product 1

HCID 67085451HCID 67085451, compoundYield 71.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

The compound of formula (V) obtained in Example 1-7 (3.2 g, 4.12 mmol) was dissolved in anhydrous tetrahydrofuran (32 ml). To the resulting solution, 1 M tetrabutyl ammonium fluoride solution in tetrahydrofuran (8.24 mL, 8.24 mmol) was added and stirred at room temperature for 13 hrs. After completion of the reaction, the resulting mixture was quenched by adding distilled water (30 ml). The solution thus obtained was extracted with ethyl acetate (30 ml), dried over anhydrous sodium sulfate, filtered, and condensed. The resulting material was stirred in methanol (32 ml) to obtain the title compound (1.6 g, yield: 71.6%).

Workup

  1. customAfter completion of the reaction
  2. customthe resulting mixture was quenched
  3. additionby adding
  4. distillationdistilled water (30 ml)
  5. customThe solution thus obtained
  6. extractionwas extracted with ethyl acetate (30 ml)
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. customcondensed

Sources & evidence

ORD record
ord-9ee2a1016dbc40ea8d968bec94b35c84
Source dataset
uspto-grants-2013_10
Patent number
US08569491B2

Reaction notes

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