Triethylamine → HCID 11573873, compound

HRID 1454805Notes

Reaction equation

O=[C:2]1[CH2:7][C@H:6]([NH:8]C(=O)OC(C)(C)C)[C@@H:5]([C:16]2[CH:21]=[C:20]([F:22])[C:19]([F:23])=[CH:18][C:17]=2[F:24])[CH2:4][CH2:3]1.Cl.[N:26]1[CH:27]=[N:28][N:29]2[CH2:34][CH2:33][NH:32][CH2:31][C:30]=12.C(N(CC)CC)C.[B][B][B][B][B][B][B][B][B][B]>CO>[N:26]1[CH:27]=[N:28][N:29]2[CH2:34][CH2:33][N:32]([C@@H:2]3[CH2:7][C@H:6]([NH2:8])[C@@H:5]([C:16]4[CH:21]=[C:20]([F:22])[C:19]([F:23])=[CH:18][C:17]=4[F:24])[CH2:4][CH2:3]3)[CH2:31][C:30]=12

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of tert-butyl [(1S,2R)-5-oxo-2-(2,4,5-trifluorophenyl)cyclohexyl]carbamate (Intermediate 1, 200mg) in anhydrous methanol (8.0 mL) under nitrogen was added 5,6,7,8-tetrahydro[1,2,4]triazolo[1,5-a]pyrazine hydrochloride (55 mg), triethylamine (0.081 mL) and decaborane (22 mg). After stirring at 50° C. for 24 h, the reaction mixture was concentrated and chromatographed by preparative TLC (silica gel, 1:4:95 ammonium hydroxide/methanol/dichloromethane). The slow moving desired compound was recovered, stirred in 4N hydrogen chloride in 1,4-dioxane for 50 min, and concentrated. The residue was purified by preparative TLC (silica, 1:9:90 ammonium hydroxide/methanol/dichloromethane) to afford the title compound. LC-MS 352.1 (M+1).

Workup

concentrationthe reaction mixture was concentrated
customchromatographed by preparative TLC (silica gel, 1:4:95 ammonium hydroxide/methanol/dichloromethane)
customThe slow moving desired compound was recovered
stirringstirred in 4N hydrogen chloride in 1,4-dioxane for 50 min
concentrationconcentrated
customThe residue was purified by preparative TLC (silica, 1:9:90 ammonium hydroxide/methanol/dichloromethane)

Sources & evidence

ORD record: ord-ea9b73794d87480c8cef9d4c51e621dc
Source dataset: uspto-grants-2009_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07482336B2

Reaction notes

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