Tetrabutylammonium Fluoride → HCID 121268904, compound

HRID 2199633Notes

Reaction equation

HRID 2199633 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[C:9][C:10]2[CH:11]=[C:12]([NH:16][C:17]([NH:19][C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([C:27]([F:30])([F:29])[F:28])[CH:21]=3)=[O:18])[CH:13]=[CH:14][CH:15]=2)=[CH:6][C:5]([C:31]2[N:32]=[N:33][N:34]([CH2:36][CH2:37][CH2:38][O:39][Si](C(C)(C)C)(C)C)[N:35]=2)=[CH:4][N:3]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[NH2:1][C:2]1[C:7]([C:8]#[C:9][C:10]2[CH:11]=[C:12]([NH:16][C:17]([NH:19][C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([C:27]([F:30])([F:28])[F:29])[CH:21]=3)=[O:18])[CH:13]=[CH:14][CH:15]=2)=[CH:6][C:5]([C:31]2[N:32]=[N:33][N:34]([CH2:36][CH2:37][CH2:38][OH:39])[N:35]=2)=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 131735700HCID 131735700, compound

Product 1

HCID 121268904HCID 121268904, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the solution of 1-(3-((2-amino-5-(2-(3-((tert-butyldimethylsilyl)oxy)propyl)-2H-tetrazol-5-yl)pyridin-3-yl)ethynyl)phenyl)-3-(4-chloro-3-(trifluoromethyl)phenyl)urea (188 mg, 0.28 mmol, 1 eq) in anhydrous tetrahydrofuran (5 mL) under nitrogen atmosphere at 0° C. was added dropwise tetrabutylammonium fluoride (1.0 M in THF, 0.84 mL, 3 eq). The reaction was stirred at room temperature for 3 hours and then concentrated and loaded onto silica. The mixture was subject to a column chromatography (EtOAc-Hex 4:1 to MeOH-EtOAc 1:25) to yield 1-[3-({2-amino-5-[2-(3-hydroxypropyl)-2H-tetrazol-5-yl]pyridin-3-yl}ethynyl)phenyl]-3-[4-chloro-3-(trifluoromethyl)phenyl]urea as a white solid in the amount of 127 mg.

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-a186beafebf44c48825ad5aa0fc96abd
Source dataset
uspto-grants-2016_06
Patent number
US09359336B2

Reaction notes

Loading…