Trifluoroacetic acid → HCID 44180766, compound

HRID 564595Notes

Reaction equation

HRID 564595 reaction equation
[CH2:1]([N:3]1[C:7]2=[N:8][C:9]([CH2:61][CH3:62])=[C:10]([CH2:19][N:20]([CH3:60])[C:21]([C:23]3[CH:24]=[C:25]([C:29]([NH:31][CH2:32][C:33]4[CH:34]=[CH:35][C:36]([F:59])=[C:37]([C:39]5[CH:44]=[CH:43][CH:42]=[C:41]([CH2:45][N:46]6[CH2:51][CH2:50][N:49](C(OC(C)(C)C)=O)[CH2:48][CH2:47]6)[CH:40]=5)[CH:38]=4)=[O:30])[CH:26]=[CH:27][CH:28]=3)=[O:22])[C:11]([NH:12][CH:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)=[C:6]2[CH:5]=[N:4]1)[CH3:2].C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH2:1]([N:3]1[C:7]2=[N:8][C:9]([CH2:61][CH3:62])=[C:10]([CH2:19][N:20]([CH3:60])[C:21]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([NH:31][CH2:32][C:33]4[CH:38]=[C:37]([C:39]5[CH:44]=[CH:43][CH:42]=[C:41]([CH2:45][N:46]6[CH2:47][CH2:48][NH:49][CH2:50][CH2:51]6)[CH:40]=5)[C:36]([F:59])=[CH:35][CH:34]=4)=[O:30])[CH:24]=3)=[O:22])[C:11]([NH:12][CH:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)=[C:6]2[CH:5]=[N:4]1)[CH3:2]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 57813475HCID 57813475, compound

Product 1

HCID 44180766HCID 44180766, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1,1-dimethylethyl 4-{[5′-({[(3-{[{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}(methyl)amino]carbonyl}phenyl) carbonyl]amino}methyl)-2′-fluoro-3-biphenylyl]methyl}-1-piperazinecarboxylate (0.056 g, 0.066 mmol) in DCM (0.25 mL) was added TFA (0.25 mL) which was then stirred at room temperature for 30 min before being diluted with DCM and basified with NaHCO3 (sat. aq.). The organic layer was separated, dried over Na2SO4, filtered, concentrated, purified using a Gilson HPLC (with TFA), and the final product was basified with an amine cartridge to afford 0.047 g (95%) of the title compound. LC-MS m/z 747 (M+H)+; 1H-NMR (400 MHz, CD3OD) δ ppm 1.39 (t, J=7.53 Hz, 3 H) 1.50 (t, J=7.28 Hz, 3 H) 1.79-1.92 (m, 2 H) 2.08-2.17 (m, J=12.80, 1.76 Hz, 2 H) 2.93 (s, 3 H) 3.15 (q, J=7.45 Hz, 2 H) 3.56 (s, 8 H) 3.62-3.71 (m, 2 H) 3.98-4.06 (m, J=8.66, 2.89 Hz, 2 H) 4.33-4.42 (m, 1 H) 4.45-4.54 (m, 4 H) 4.61 (s, 2 H) 7.17 (dd, J=10.54, 8.53 Hz, 1 H) 7.38-7.44 (m, J=5.52, 3.01 Hz, 1 H) 7.49-7.63 (m, 4 H) 7.64-7.70 (m, 2 H) 7.74 (s, 1 H) 7.97-8.03 (m, 2 H) 8.32 (s, 1 H).

Workup

  1. customThe organic layer was separated
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified

Sources & evidence

ORD record
ord-39eaf51195924bc093a0707ae0d77d20
Source dataset
uspto-grants-2011_11
Patent number
US08067408B2

Reaction notes

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