Tetrabutylammonium Fluoride → HCID 67202653, compound

HRID 1888534Notes

Reaction equation

HRID 1888534 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-65578ab855e348bc9589132360f26551
Source dataset
uspto-grants-2013_08
Patent number
US08501765B2

Reaction notes

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