Tetrahydrofuran → HCID 89662807, compound

HRID 1479106Notes

Reaction equation

HRID 1479106 reaction equation
C([Si](C)(C)[O:6][CH2:7][CH2:8][N:9]([CH3:36])[CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19]([N:21]1[CH2:35][C:24]2=[C:25]3[N:30]([N:31]=[C:23]2[CH2:22]1)[C:29]([CH3:32])=[C:28]([Cl:33])[C:27]([CH3:34])=[N:26]3)=[O:20])(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1>CC(=O)OCC>[Cl:33][C:28]1[C:27]([CH3:34])=[N:26][C:25]2[N:30]([N:31]=[C:23]3[CH2:22][N:21]([C:19]([C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=4[O:12][CH2:11][CH2:10][N:9]([CH2:8][CH2:7][OH:6])[CH3:36])=[O:20])[CH2:35][C:24]3=2)[C:29]=1[CH3:32]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 131736562HCID 131736562, compound

Product 1

HCID 89662807HCID 89662807, compoundYield 38.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of [2-(2-{[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-methyl-amino}-ethoxy)-phenyl]-(6-chloro-5,7-dimethyl-1H,3H-2,4,7a,8-tetraaza-cyclopenta[a]inden-2-yl)-methanone (40 mg; 0.07 mmol; 1 eq.) and a 1M solution of tetrabutyl-ammonium fluoride in THF (0.09 mL; 0.09 mmol; 1.2 eq.) was stirred at room temperature for 3 hours. The solution was diluted with EA, washed with water, dried over magnesium sulfate and concentrated in vacuo. Purification by column chromatography (EA to 20% MeOH in EA) afforded the title compound (12 mg, 38%) as a colourless oil. HPLC (max plot) 95.8%, Rt 2.56 min. UPLC/MS: (MS+) 444.3 ([M+H]+).

Workup

  1. washwashed with water
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customPurification by column chromatography (EA to 20% MeOH in EA)

Sources & evidence

ORD record
ord-54fb7fbd2d5e42a9a1cbb67c81a49908
Source dataset
uspto-grants-2016_08
Patent number
US09403835B2

Reaction notes

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