Tetrahydrofuran → HCID 178438600, compound

HRID 519604Notes

Reaction equation

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

Participants

Conditions

Temperature: 70 °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}biphenyl-2-carbonitrile (3.7 g), sodium cyanoborohydride (1.3 g), boron trifluoride-diethyl ether complex (2.5 mL) and tetrahydrofuran (50 mL) was stirred at 70° C. for 16 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, and the residue was purified by silica gel column chromatography to give the title compound as a colorless solid (1.8 g, 47%).

Workup

washwashed with water
dry with materialwith saturated brine, and dried over anhydrous magnesium sulfate
customThe solvent was evaporated under reduced pressure
customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-c9af371ca3e94e5caca09f1861f3a6b2
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115136B2

Reaction notes

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