Diisopropylethylamine → HCID 59437531, compound

HRID 2382886Notes

Reaction equation

HRID 2382886 reaction equation
Br[C:2]1[N:7]2[N:8]=[C:9]([NH:11][C:12](=[O:21])[C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=3)[N:10]=[C:6]2[CH:5]=[CH:4][CH:3]=1.C([N:25]([CH:28]([CH3:30])[CH3:29])CC)(C)C>C(O)CCC>[OH:19][CH:15]1[CH2:16][CH2:29][CH:28]([NH:25][C:2]2[N:7]3[N:8]=[C:9]([NH:11][C:12](=[O:21])[C:13]4[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=4)[N:10]=[C:6]3[CH:5]=[CH:4][CH:3]=2)[CH2:30][CH2:14]1

Participants

4

Reactant 2

HCID 81531DiisopropylethylamineHCID 86643870HCID 86643870, compound

Product 1

HCID 59437531HCID 59437531, compoundYield 72.1%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A sealed vessel containing N-(5-bromo-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-3-methoxybenzamide (69 mg, 0.20 mmol, 1 mol eq.), trans-aminocyclohexanol (35 mg, 0.30 mmol, 1.5 mol eq.), di-iso-propylethylamine (60 μL, 0.32 mmol, 1.6 mol eq.) and n-butanol (0.75 mL) was irradiated at 220° C., with stirring, for 20 minutes. The solvent was removed in vacuo and the residue dissolved in DMSO (1.5 mL) and purified by reverse phase preparatory HPLC to give the title compound as a beige solid (27.5 mg, 36%). HPLC, Rt: 1.86 min (purity: 100%). LC/MS M+(ESI): 382.3, M−(ESI) 380.3.

Workup

  1. customwas irradiated at 220° C.
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue dissolved in DMSO (1.5 mL)
  4. custompurified by reverse phase preparatory HPLC

Sources & evidence

ORD record
ord-d22a806d6e6946d2b953be8c28d148f7
Source dataset
uspto-grants-2012_09
Patent number
US08263595B2

Reaction notes

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