Triethylamine → HCID 178490778, compound

HRID 1639961Notes

Reaction equation

HRID 1639961 reaction equation
Cl.[OH:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([N:9]2[CH2:13][CH2:12][C:11]3([CH2:18][CH2:17][CH2:16][NH:15][CH2:14]3)[C:10]2=[O:19])[CH2:5][CH2:4]1.Br[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH3:28])[N:22]=1.C(N(CC)CC)C.CN1CCCC1=O>[Cu]I>[OH:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([N:9]2[CH2:13][CH2:12][C:11]3([CH2:18][CH2:17][CH2:16][N:15]([C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH3:28])[N:22]=4)[CH2:14]3)[C:10]2=[O:19])[CH2:5][CH2:4]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 13387N-methyl-2-pyrrolidoneHCID 2568102-Bromo-6-methoxypyridineHCID 178479652HCID 178479652, compound

Product 1

HCID 178490778HCID 178490778, compoundYield 19.2%

Reagents, catalysts & solvents 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst

Procedure

A mixture of 2-(trans-4-hydroxycyclohexyl)-2,7-diazaspiro[4.5]decan-1-one hydrochloride (35 mg, 0.00012 mol), 2-bromo-6-methoxypyridine (34 mg, 0.00018 mol), triethylamine (200 μL, 0.001 mol), and copper(I) iodide (28 mg, 0.00014 mol) in N-methylpyrrolidinone (1.0 mL, 0.010 mol) was microwave irradiated at 180° C. for 20 min. After allowing the reaction mixture to cool to rt the crude mixture was purified by prep.-HPLC to afford 8.3 mg of the desired product. LC-MS: 360.3 (M+H)+.

Workup

  1. customwas microwave irradiated at 180° C. for 20 min
  2. customwas purified by prep.-HPLC

Sources & evidence

ORD record
ord-3f46c84e3c74465eb9cae05e915182b5
Source dataset
uspto-grants-2012_02
Patent number
US08110581B2

Reaction notes

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