Tetrabutylammonium Fluoride → HCID 67202653, compound

HRID 1505995Notes

Reaction equation

HRID 1505995 reaction equation
C1(S([N:10]2[C:14]3[CH:15]=[N:16][C:17]([C:31]#[N:32])=[C:18]([CH2:19][CH:20]4[CH2:25][CH2:24][N:23]([CH2:26][C:27]([F:30])([F:29])[F:28])[CH2:22][CH2:21]4)[C:13]=3[C:12]3[CH:33]=[CH:34][CH:35]=[N:36][C:11]2=3)(=O)=O)C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>>[F:30][C:27]([F:28])([F:29])[CH2:26][N:23]1[CH2:22][CH2:21][CH:20]([CH2:19][C:18]2[C:13]3[C:12]4[CH:33]=[CH:34][CH:35]=[N:36][C:11]=4[NH:10][C:14]=3[CH:15]=[N:16][C:17]=2[C:31]#[N:32])[CH2:25][CH2:24]1

Participants

3

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 67027535HCID 67027535, compound

Product 1

HCID 67202653HCID 67202653, compoundYield 80.3%

Procedure

9-Benzenesulfonyl-5-[1-(2,2,2-trifluoroethyl)-piperidin-4-ylmethyl]-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carbonitrile (0.16 g, 0.3 mmol) was dissolved in tetrabutylammonium fluoride (1M in THF, 5 mL, 5 mmol) and stirred at ambient temperature for 24 h. The solution was filtered through 2 g NH2 cartridge, eluting with 1:1 methanol/dichloromethane. The filtrate was concentrated in vacuo and the residue diluted with water (10 mL) and the resultant precipitate collected by filtration. Purification of the solid by flash chromatography (silica, 5 g column, SPE Si-II, 0-6% methanol in DCM) afforded the title compound as a white solid (90 mg, 80%). 1H NMR (DMSO-D6, 400 MHz): 12.88 (s, 1H), 8.91 (s, 1H), 8.72-8.64 (m, 2H), 7.46 (dd, J=8.0, 4.8 Hz, 1H), 3.09 (q, J=10.3 Hz, 2H), 2.92-2.83 (m, 2H), 2.25-2.15 (m, 2H), 1.85-1.72 (m, 1H), 1.66-1.58 (m, 2H), 1.57-1.43 (m, 2H). LCMS (Method H): RT=9.20 min, M+H+=374.

Workup

  1. filtrationThe solution was filtered through 2 g NH2 cartridge
  2. washeluting with 1:1 methanol/dichloromethane
  3. concentrationThe filtrate was concentrated in vacuo
  4. additionthe residue diluted with water (10 mL)
  5. filtrationthe resultant precipitate collected by filtration
  6. customPurification of the solid by flash chromatography (silica, 5 g column, SPE Si-II, 0-6% methanol in DCM)

Sources & evidence

ORD record
ord-9150f515df37403289a20c24aab7a576
Source dataset
uspto-grants-2015_12
Patent number
US09216980B2

Reaction notes

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