Tetrabutylammonium Fluoride → 1-(6-(5-cyanopyrazin-2-ylamino)-4-(piperidin-3-ylmethylamino)pyridin-3-yl)-N-(2-hydroxyethyl)-1H-pyrrole-3-carboxamide

HRID 556830Notes

Reaction equation

HRID 556830 reaction equation
[Si]([O:8][CH2:9][CH2:10][NH:11][C:12]([C:14]1[CH:18]=[CH:17][N:16]([C:19]2[C:20]([NH:34][CH2:35][CH:36]3[CH2:41][CH2:40][CH2:39][N:38](C(OC(C)(C)C)=O)[CH2:37]3)=[CH:21][C:22]([NH:25][C:26]3[CH:31]=[N:30][C:29]([C:32]#[N:33])=[CH:28][N:27]=3)=[N:23][CH:24]=2)[CH:15]=1)=[O:13])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[C:32]([C:29]1[N:30]=[CH:31][C:26]([NH:25][C:22]2[N:23]=[CH:24][C:19]([N:16]3[CH:17]=[CH:18][C:14]([C:12]([NH:11][CH2:10][CH2:9][OH:8])=[O:13])=[CH:15]3)=[C:20]([NH:34][CH2:35][CH:36]3[CH2:41][CH2:40][CH2:39][NH:38][CH2:37]3)[CH:21]=2)=[N:27][CH:28]=1)#[N:33]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 66745676tert-butyl 3-((5-(3-(2-(tert-butyldimethylsilyloxy)ethylcarbamoyl)-1H-pyrrol-1-yl)-2-(5-cyanopyrazin-2-ylamino)pyridin-4-ylamino)methyl)piperidine-1-carboxylate

Product 1

HCID 596135181-(6-(5-cyanopyrazin-2-ylamino)-4-(piperidin-3-ylmethylamino)pyridin-3-yl)-N-(2-hydroxyethyl)-1H-pyrrole-3-carboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

tert-Butyl 3-((5-(3-(2-(tert-butyldimethylsilyloxy)ethylcarbamoyl)-1H-pyrrol-1-yl)-2-(5-cyanopyrazin-2-ylamino)pyridin-4-ylamino)methyl)piperidine-1-carboxylate (80 mg, 0.118 mmol) was dissolved in THF (2 mL) and tetrabutylammonium fluoride on silica (1.5 mmol/g; 237 mg, 0.355 mmol) was added. The reaction mixture was stirred for 1 h at room temperature. The mixture was filtered and the solvent was evaporated. The residue was dissolved in methanol (1 mL) and absorbed on to a TsOH solidphase extraction cartridge. After 1.5 h the cartridge was eluted with 7M ammonia in methanol. The eluent was evaporated to dryness and the residue was purified by HPLC to give 1-(6-(5-cyanopyrazin-2-ylamino)-4-(piperidin-3-ylmethylamino)pyridin-3-yl)-N-(2-hydroxyethyl)-1H-pyrrole-3-carboxamide.

Workup

  1. filtrationThe mixture was filtered
  2. customthe solvent was evaporated
  3. dissolutionThe residue was dissolved in methanol (1 mL)
  4. customabsorbed on to a TsOH solidphase extraction cartridge
  5. washAfter 1.5 h the cartridge was eluted with 7M ammonia in methanol
  6. customThe eluent was evaporated to dryness
  7. customthe residue was purified by HPLC

Sources & evidence

ORD record
ord-c0812e41f32f406b88b860f07c97f9c5
Source dataset
uspto-grants-2011_11
Patent number
US08058045B2

Reaction notes

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