Tetrabutylammonium Fluoride → HCID 178508367, compound

HRID 389501Notes

Reaction equation

HRID 389501 reaction equation
[Si]([O:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([N:15]2[CH:19]=[C:18]([C:20]3[CH:25]=[N:24][C:23]([NH2:26])=[C:22]4[O:27][C:28]([C:30]5[CH:39]=[CH:38][CH:37]=[C:36]6[C:31]=5[CH:32]=[CH:33][N:34]=[CH:35]6)=[CH:29][C:21]=34)[CH:17]=[N:16]2)[CH2:11][CH2:10]1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[NH2:26][C:23]1[N:24]=[CH:25][C:20]([C:18]2[CH:17]=[N:16][N:15]([C@H:12]3[CH2:11][CH2:10][C@H:9]([OH:8])[CH2:14][CH2:13]3)[CH:19]=2)=[C:21]2[CH:29]=[C:28]([C:30]3[CH:39]=[CH:38][CH:37]=[C:36]4[C:31]=3[CH:32]=[CH:33][N:34]=[CH:35]4)[O:27][C:22]=12

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 178455332HCID 178455332, compound

Product 1

HCID 178508367HCID 178508367, compoundYield 28.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-[1-(trans-4-{[tert-butyl(dimethyl)silyl]oxy}cyclohexyl)-1H-pyrazol-4-yl]-2-(isoquinolin-5-yl)furo[2,3-c]pyridin-7-amine (25 mg, 0.046 mmol) was dissolved in THF (1.00 mL) and tetra-n-butylammonium fluoride (1.0 M in THF, 1.00 mL, 1.00 mmol) was added and stirred at RT for 16 h. The reaction was then washed with sodium bicarbonate and water (2×). The organic layer was collected, dried over sodium sulfate, filtered, and then concentrated in vacuo to a solid. Purification by flash chromatography (0 to 5% 7 N NH3/MeOH:EtOAc) afforded 5.5 mg (28%) of the title compound. 1H NMR (400 MHz, CD3OD): δ 9.33 (d, J=0.51 Hz, 1H), 8.57 (d, J=6.06 Hz, 1H), 8.49 (d, J=6.06 Hz, 1H), 8.35 (dd, J=7.33, 1.26 Hz, 1H), 8.24 (d, J=8.08 Hz, 1H), 8.11 (s, 1H), 7.92 (s, 1H), 7.90 (d, J=0.76 Hz, 1H), 7.83 (dd, J=8.21, 7.45 Hz, 1H), 7.50 (s, 1 H), 4.25 (tt, J=11.84, 3.82 Hz, 1H), 3.69 (tt, J=10.89, 4.26 Hz, 1H), 2.07-2.22 (m, 4H), 1.95-2.05 (m, 2H), 1.45-1.57 (m, 2H); MS (ESI): 427.19 [M+H]+; HPLC tR=0.87 min (TOF: polar—3 min).

Workup

  1. washThe reaction was then washed with sodium bicarbonate and water (2×)
  2. customThe organic layer was collected
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo to a solid
  6. customPurification by flash chromatography (0 to 5% 7 N NH3/MeOH:EtOAc)

Sources & evidence

ORD record
ord-c5eeaa49ee4a4a8bb12220998ff3e045
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

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