2,2,2-Trifluoroethyl trifluoromethanesulfonate → HCID 67027535, compound

HRID 1888533Notes

Reaction equation

HRID 1888533 reaction equation
C(N(CC)C(C)C)(C)C.[F:10][C:11]([F:22])([F:21])[CH2:12]OS(C(F)(F)F)(=O)=O.[C:23]1([S:29]([N:32]2[C:36]3[CH:37]=[N:38][C:39]([C:48]#[N:49])=[C:40]([CH2:41][CH:42]4[CH2:47][CH2:46][NH:45][CH2:44][CH2:43]4)[C:35]=3[C:34]3[CH:50]=[CH:51][CH:52]=[N:53][C:33]2=3)(=[O:31])=[O:30])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C1COCC1>[C:23]1([S:29]([N:32]2[C:36]3[CH:37]=[N:38][C:39]([C:48]#[N:49])=[C:40]([CH2:41][CH:42]4[CH2:47][CH2:46][N:45]([CH2:12][C:11]([F:10])([F:21])[F:22])[CH2:44][CH2:43]4)[C:35]=3[C:34]3[CH:50]=[CH:51][CH:52]=[N:53][C:33]2=3)(=[O:31])=[O:30])[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 81531DiisopropylethylamineHCID 67203172HCID 67203172, compound

Product 1

HCID 67027535HCID 67027535, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

N,N-Diisopropylethylamine (100 mg, 0.77 mmol) and trifluoromethane sulfonic acid 2,2,2-trifluoroethyl ester (100 mg, 0.43 mmol) in THF (1 mL) were added to a solution of 9-benzenesulfonyl-5-piperidin-4-ylmethyl-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carbonitrile in THF (4 mL) and resultant mixture stirred at ambient temperature for 30 min. The mixture was then filtered through a 2 g SiII SPE cartridge, eluting with THF. The THF washings were concentrated in vacuo and the resultant residue was purified by flash chromatography (silica, 2 g column, Si II SPE, 0-20% ethyl acetate in DCM) to afford title compound as a white solid (0.16 g, 85%). 1H NMR (CDCl3, 400 MHz): 9.81 (d, J=2.9 Hz, 1H), 8.81-8.75 (m, 1H), 8.34 (d, J=8.1 Hz, 1H), 8.28 (d, J=7.9 Hz, 2H), 7.66-7.59 (m, 1H), 7.55-7.45 (m, 3H), 3.35-3.27 (m, 2H), 3.02-2.88 (m, 5H), 2.32-2.21 (m, 2H), 1.86-1.60 (m, 4H).

Workup

  1. filtrationThe mixture was then filtered through a 2 g SiII SPE cartridge
  2. washeluting with THF
  3. concentrationThe THF washings were concentrated in vacuo
  4. customthe resultant residue was purified by flash chromatography (silica, 2 g column, Si II SPE, 0-20% ethyl acetate in DCM)

Sources & evidence

ORD record
ord-56cb6362d2a741ad99ad94d90be15b07
Source dataset
uspto-grants-2013_08
Patent number
US08501765B2

Reaction notes

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