Sodium Thiosulfate → HCID 178438711, compound

HRID 1688601Notes

Reaction equation

[CH2:1]1[C:4]2([CH2:43][O:42][C:7]3([CH2:12][CH2:11][CH:10]([N:13]4[C:18](=[O:19])[C:17]([CH2:20][C:21]5[CH:26]=[CH:25][C:24]([C:27]6[C:28]([C:33]#[N:34])=[CH:29][CH:30]=[CH:31][CH:32]=6)=[CH:23][C:22]=5[F:35])=[C:16]([CH2:36][CH2:37][CH3:38])[N:15]5[N:39]=[CH:40][N:41]=[C:14]45)[CH2:9][CH2:8]3)[O:6][CH2:5]2)[CH2:3][CH2:2]1.[C:44]([BH3-])#N.[Na+].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O.C(=O)([O-])O.[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+].C[Mg]Br.[Cl-].[NH4+]>C(OCC)(=O)C.C(#N)C.O1CCCC1>[F:35][C:22]1[CH:23]=[C:24]([C:27]2[C:28]([C:33]#[N:34])=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:25]=[CH:26][C:21]=1[CH2:20][C:17]1[C:18](=[O:19])[N:13]([C@H:10]2[CH2:9][CH2:8][C@H:7]([O:6][CH2:5][C:4]3([CH:43]([OH:42])[CH3:44])[CH2:3][CH2:2][CH2:1]3)[CH2:12][CH2:11]2)[C:14]2[N:15]([N:39]=[CH:40][N:41]=2)[C:16]=1[CH2:36][CH2:37][CH3:38]

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 4′-{[4-(6,13-dioxadispiro[3.2.5.2]tetradec-10-yl)-5-oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl]methyl}-3′-fluorobiphenyl-2-carbonitrile (3.6 g), sodium cyanoborohydride (5.3 g), boron trifluoride-diethyl ether complex (3.1 mL) and tetrahydrofuran (150 mL) was stirred at 50° C. for 24 hr. The reaction mixture was diluted with ethyl acetate, washed with water and then with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue obtained by purification by silica gel column chromatography was dissolved in acetonitrile (30 mL), 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one (3.4 g) was added, and the mixture was stirred at room temperature for 4 hr. Saturated aqueous sodium hydrogen carbonate solution and sodium thiosulfate were added to the reaction mixture, and the mixture was stirred at room temperature for 2 hr, and extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue obtained by purification by silica gel column chromatography was dissolved in tetrahydrofuran (20 mL), and methylmagnesium bromide (1.0 M tetrahydrofuran solution, 4.5 mL) was added at room temperature. The reaction mixture was stirred for 2 hr, saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The obtained ethyl acetate layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give the title compound as a colorless solid (0.72 g, 19%).

Workup

washwashed with water
dry with materialwith saturated brine, and dried over anhydrous magnesium sulfate
customThe solvent was evaporated under reduced pressure
customThe residue obtained by purification by silica gel column chromatography
stirringthe mixture was stirred at room temperature for 4 hr
stirringthe mixture was stirred at room temperature for 2 hr
extractionextracted with ethyl acetate
washThe organic layer was washed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
customThe solvent was evaporated under reduced pressure
customThe residue obtained by purification by silica gel column chromatography
stirringThe reaction mixture was stirred for 2 hr
extractionthe mixture was extracted with ethyl acetate
washThe obtained ethyl acetate layer was washed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
customThe solvent was evaporated under reduced pressure
customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-8b935093d11f432ea53ca22750c77b58
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08148383B2

Reaction notes

Loading…