1,4-Dioxane → HCID 24758303, compound

HRID 1672393Notes

Reaction equation

HRID 1672393 reaction equation
Br[C:2]1[CH:25]=[CH:24][C:5]([CH2:6][N:7]2[C:11]3([CH2:15][CH2:14][N:13]([CH:16]4[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]4)[C:12]3=[O:22])[CH2:10][C@@H:9]([OH:23])[CH2:8]2)=[CH:4][CH:3]=1.O1CCOCC1.CN[C@H]1CCCC[C@@H]1NC.[F:42][C:43]([F:50])([F:49])[C:44]1[CH:48]=[CH:47][NH:46][N:45]=1>[Cu]I>[CH:16]1([N:13]2[CH2:14][CH2:15][C:11]3([N:7]([CH2:6][C:5]4[CH:24]=[CH:25][C:2]([N:46]5[CH:47]=[CH:48][C:44]([C:43]([F:50])([F:49])[F:42])=[N:45]5)=[CH:3][CH:4]=4)[CH2:8][C@H:9]([OH:23])[CH2:10]3)[C:12]2=[O:22])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

6

Reactant 4

HCID 312751,4-DioxaneHCID 18070343-(Trifluoromethyl)pyrazoleHCID 13822957(1S,2S)-(+)-N,N'-Dimethylcyclohexane-1,2-diamineHCID 24759198HCID 24759198, compound

Product 1

HCID 24758303HCID 24758303, compound

Reagents, catalysts & solvents 1

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

Conditions

Temperature
100 °C

Procedure

To a solution of (3R)-1-(4-bromobenzyl)-7-cyclohexyl-3-hydroxy-1,7-diazaspiro[4.4]nonan-6-one (25.0 mg, 0.0000614 mol; prepared as in Example 37) in 1,4-dioxane (0.8 mL, 0.01 mol) was added (1S,2S)—N,N′-dimethylcyclohexane-1,2-diamine (1.7 mg, 0.000012 mol), copper(I) iodide (1.2 mg, 0.0000061 mol), and 3-(trifluoromethyl)-1H-pyrazole (17 mg, 0.00012 mol). After stirring the resulting mixture at 100° C. for 16 h, the crude reaction mixture was purified by prep.-HPLC under pH=10 conditions to afford the desired product. LC-MS: 463.2 (M+1H)+.

Workup

  1. customthe crude reaction mixture
  2. customwas purified by prep.-HPLC under pH=10 conditions

Sources & evidence

ORD record
ord-744866164f4e4227a072ee5d82e6a5c5
Source dataset
uspto-grants-2011_08
Patent number
US07998959B2

Reaction notes

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