Tetrabutylammonium Fluoride → HCID 57647287, compound
Reaction equation
[CH3:1][CH:2]([CH3:34])[CH2:3][C:4]([N:6]([CH2:31][CH2:32][CH3:33])[C:7]1[S:8][CH:9]=[C:10]([C:12]2[C:13]3[CH:20]=[CH:19][N:18](S(C4C=CC(C)=CC=4)(=O)=O)[C:14]=3[N:15]=[CH:16][N:17]=2)[N:11]=1)=[O:5].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH3:1][CH:2]([CH3:34])[CH2:3][C:4]([N:6]([CH2:31][CH2:32][CH3:33])[C:7]1[S:8][CH:9]=[C:10]([C:12]2[C:13]3[CH:20]=[CH:19][NH:18][C:14]=3[N:15]=[CH:16][N:17]=2)[N:11]=1)=[O:5]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
To 55 mg [0.11 mmol] of 3-Methyl-N-propyl-N-{4-[7-(toluene-4-sulfonyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-thiazol-2-yl}-butyramide dissolved in 2 mL of dry THF was added 5 drops of a 1M tetra n-butylammonium fluoride solution in THF, the vial was capped and heated/stirred at 80° C. for 4 hours. Reaction determined to be complete via HPLC and reaction was cooled. The solvent was removed under an N2 stream and residue was partitioned between DCM and water. The organic layer was brined and dried with anhydrous sodium sulphate and the solvent removed under vacuum. The crude product was purified on C18 silica with water/acetonitrile/TFA as the eluent, isolating 15 mg of a yellow solid which constituted a 39% yield.
Workup
- customthe vial was capped
- customReaction
- customto be complete via HPLC and reaction
- temperaturewas cooled
- customThe solvent was removed under an N2 stream and residue
- customwas partitioned between DCM and water
- dry with materialdried with anhydrous sodium sulphate
- customthe solvent removed under vacuum
- customThe crude product was purified on C18 silica with water/acetonitrile/TFA as the eluent
Sources & evidence
- ORD record
- ord-c46a2c32db2e468b967cc0a0d292c1fa
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08741912B2
Reaction notes
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