Triethylamine → Ammonia

HRID 2383364Notes

Reaction equation

[CH:1]1([C@@:7]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([C:9]2[N:13]=[CH:12][N:11]([CH2:14][CH:15]3[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]3)[N:10]=2)[OH:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Br[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][N:37]([C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])[C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39].C(N(CC)CC)C>C(#N)C>[NH3:10].[C:41]([O:40][C:38]([N:37]([CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][N:18]1[CH2:19][CH2:20][CH:15]([CH2:14][N:11]2[CH:12]=[N:13][C:9]([C@:7]([CH:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)([OH:8])[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[N:10]2)[CH2:16][CH2:17]1)[C:45]([O:47][C:48]([CH3:49])([CH3:50])[CH3:51])=[O:46])=[O:39])([CH3:44])([CH3:43])[CH3:42]

Participants

Conditions

Temperature: 50 °C

Procedure

(R)-cyclohexyl(phenyl)[1-(piperidin-4-ylmethyl)-1H-1,2,4-triazol-3-yl]methanol (Preparation 4, 2.00 g, 5.64 mmol) and di-tert-butyl (9-bromononyl)imidodicarbonate (U.S. Pat. No. 4,167,167, 2.38 g, 5.64 mmol) were dissolved in acetonitrile (60 ml) and triethylamine (2.35 ml, 16.9 mmol) added. After stirring at 50° C. for 18 hours, the solvent was removed in vacuo, and the residue purified by column chromatography on silica gel eluting with dichloromethane:methanol:880 ammonia (98:2:0.2, by volume) to furnish the title compound as a clear oil, in 60% yield, 2.6 g (contains 10% of other triazole regio-isomer)

Workup

customthe solvent was removed in vacuo
customthe residue purified by column chromatography on silica gel eluting with dichloromethane

Sources & evidence

ORD record: ord-b2d6da3fcc5841689dd3fbf59769be9d
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08263623B2

Reaction notes

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