Tetrabutylammonium Fluoride → HCID 86708501, compound

HRID 921649Notes

Reaction equation

HRID 921649 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[Cl:19][C:20]1[C:25]([NH:26][C:27]2[N:32]=[C:31]([NH:33][CH:34]3[CH2:36][CH2:35]3)[C:30]3=[N:37][CH:38]=[C:39]([C:40]#[N:41])[N:29]3[N:28]=2)=[CH:24][C:23]([C:42]#[N:43])=[CH:22][C:21]=1[N:44]1[CH2:49][CH2:48][C@@H:47]([NH:50][S:51]([CH3:54])(=[O:53])=[O:52])[C@H:46]([O:55][Si](C(C)C)(C(C)C)C(C)C)[CH2:45]1>C1COCC1>[Cl:19][C:20]1[C:25]([NH:26][C:27]2[N:32]=[C:31]([NH:33][CH:34]3[CH2:35][CH2:36]3)[C:30]3=[N:37][CH:38]=[C:39]([C:40]#[N:41])[N:29]3[N:28]=2)=[CH:24][C:23]([C:42]#[N:43])=[CH:22][C:21]=1[N:44]1[CH2:49][CH2:48][C@@H:47]([NH:50][S:51]([CH3:54])(=[O:53])=[O:52])[C@H:46]([OH:55])[CH2:45]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86708500HCID 86708500, compound

Product 1

HCID 86708501HCID 86708501, compoundYield 96.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

TBAF (1M in THF, 0.048 mL, 0.048 mmol) was added to a solution of N-((3R,4R)-1-(2-chloro-5-cyano-3-((7-cyano-4-(cyclopropylamino)imidazo[2,1-f][1,2,4]triazin-2-yl)amino)phenyl)-3-((triisopropylsilyl)oxy)piperidin-4-yl)methanesulfonamide (28 mg, 0.040 mmol) in THF (2 mL) and the reaction mixture was stirred at room temperature overnight. Solvent was evaporated and the crude product was purified by flash chromatography on silica gel using an automated ISCO system (12 g column, eluting with 0-6% methanol/dichloromethane). N-((3R,4R)-1-(2-chloro-5-cyano-3-((7-cyano-4-(cyclopropylamino)imidazo[2,1-f][1,2,4]triazin-2-yl)amino)phenyl)-3-hydroxypiperidin-4-yl)methanesulfonamide (21 mg) was obtained as a white solid.

Workup

  1. customSolvent was evaporated
  2. customthe crude product was purified by flash chromatography on silica gel using
  3. washan automated ISCO system (12 g column, eluting with 0-6% methanol/dichloromethane)

Sources & evidence

ORD record
ord-706c9c75586c4f4ea51272bbd742989e
Source dataset
uspto-grants-2016_03
Patent number
US09273057B2

Reaction notes

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