Tetrabutylammonium Fluoride → HCID 178521331, compound

HRID 1623307Notes

Reaction equation

HRID 1623307 reaction equation
[Si]([O:8][CH2:9][CH2:10][NH:11][C@H:12]1[CH2:17][CH2:16][C@H:15]([NH:18][C:19]2[CH:24]=[C:23]([C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([NH:31][CH2:32][C:33]4[CH:38]=[CH:37][CH:36]=[C:35]([F:39])[CH:34]=4)[N:26]=3)[C:22]([Cl:40])=[CH:21][N:20]=2)[CH2:14][CH2:13]1)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[Cl:40][C:22]1[C:23]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([NH:31][CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[C:35]([F:39])[CH:34]=3)[N:26]=2)=[CH:24][C:19]([NH:18][C@H:15]2[CH2:14][CH2:13][C@H:12]([NH:11][CH2:10][CH2:9][OH:8])[CH2:17][CH2:16]2)=[N:20][CH:21]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 178455267HCID 178455267, compound

Product 1

HCID 178521331HCID 178521331, compoundYield 9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a scintillation vial containing N2′-(trans-4-(2-(tert-butyldimethylsilyloxy)ethylamino)cyclohexyl)-5′-chloro-N6-(3-fluorobenzyl)-2,4′-bipyridine-2′,6-diamine from step 1) was added THF (0.300 ml) and TBAF (0.160 ml, 0.319 mmol). The homogenous reaction mixture was capped, and stirred at ambient temperature for 3 hours. The reaction mixture was concentrated and purified by reverse phase preparative HPLC to yield 2-(trans-4-(5′-chloro-6-(3-fluorobenzylamino)-2,4′-bipyridin-2′-yl-amino)cyclohexylamino)ethanol (2.2 mg, 9%). LCMS (m/z): 470.3 (MH retention time=0.58 min as a TFA salt after lypholyzing. 1H NMR (400 MHz, METHANOL-d4) δ ppm 1.31-1.46 (m, 2H) 1.51-1.67 (m, 1H) 2.21 (d, J=10.56 Hz, 2H) 3.11-3.20 (m, 2H) 3.66-3.77 (m, 1H) 3.77-3.83 (m, 1H) 4.62 (s, 1H) 6.74 (s, 1H) 6.78-6.84 (m, 1H) 6.87-6.92 (m, 1H) 6.96-7.03 (m, 1H) 7.08-7.14 (m, 1H) 7.15-7.21 (m, 1H) 7.31-7.38 (m, 1H) 7.68-7.76 (m, 1H) 8.02 (s, 1H).

Workup

  1. customThe homogenous reaction mixture was capped
  2. concentrationThe reaction mixture was concentrated
  3. custompurified by reverse phase preparative HPLC

Sources & evidence

ORD record
ord-d57eb41b94ca4fd1a5cb91ab9a2634f2
Source dataset
uspto-grants-2014_07
Patent number
US08778951B2

Reaction notes

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