Tetrabutylammonium Fluoride → HCID 58113904, compound

HRID 1046454Notes

Reaction equation

HRID 1046454 reaction equation
[CH3:1][C:2]([CH3:44])([CH3:43])[C:3]#[C:4][C:5]1[S:9][C:8]([C:10]([OH:12])=[O:11])=[C:7]([N:13]([C:34]([CH:36]2[CH2:41][CH2:40][CH:39]([CH3:42])[CH2:38][CH2:37]2)=[O:35])[CH:14]2[CH2:19][CH2:18][CH:17]([O:20][C:21]3[N:26]=[C:25]([O:27]CC[Si](C)(C)C)[CH:24]=[CH:23][N:22]=3)[CH2:16][CH2:15]2)[CH:6]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH3:1][C:2]([CH3:43])([CH3:44])[C:3]#[C:4][C:5]1[S:9][C:8]([C:10]([OH:12])=[O:11])=[C:7]([N:13]([C:34]([CH:36]2[CH2:37][CH2:38][CH:39]([CH3:42])[CH2:40][CH2:41]2)=[O:35])[CH:14]2[CH2:15][CH2:16][CH:17]([O:20][C:21]3[NH:26][C:25](=[O:27])[CH:24]=[CH:23][N:22]=3)[CH2:18][CH2:19]2)[CH:6]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium Fluoride2×HCID 58113903HCID 58113903, compound

Product 1

HCID 58113904HCID 58113904, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-(3,3-Dimethyl-but-1-ynyl)-3-((4-methyl-cyclohexanecarbonyl)-{4-[4-(2-trimethylsilanyl-ethoxy)-pyrimidin-2-yloxy]-cyclohexyl}-amino)-thiophene-2-carboxylic acid (37 mg, 0.058 mmol) in THF (1 mL) was treated with tetrabutylammonium fluoride (0.087 mL, 1M in THF, 0.087 mmol) and stirred at ambient temperature for 1.5 h. An additional portion of tetrabutylammonium fluoride (0.290 mL) was added and the reaction mixture was stirred at ambient temperature for 3 h. After concentration the residue was purified by HPLC with CH3CN (0.1% TFA)/H2O (0.1% TFA) to afford 18 mg (58% yield) of Compound 326: MS (m/z): 537.9 [M+H]−; HPLC retention time 4.28 min (2-98% acetonitrile:water with 0.05% trifluoroacetic acid).

Workup

  1. stirringthe reaction mixture was stirred at ambient temperature for 3 h
  2. concentrationAfter concentration the residue
  3. customwas purified by HPLC with CH3CN (0.1% TFA)/H2O (0.1% TFA)

Sources & evidence

ORD record
ord-a921c6b33d0445298b5003508d3ae055
Source dataset
uspto-grants-2013_10
Patent number
US08569302B2

Reaction notes

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