Pyrazole → HCID 178517862, compound

HRID 1640002Notes

Reaction equation

HRID 1640002 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]([N:8]2[CH2:25][CH2:24][CH2:23][C@@:10]3([C:14](=[O:15])[N:13]([C@H:16]4[CH2:21][CH2:20][C@@H:19]([OH:22])[CH2:18][CH2:17]4)[CH2:12][CH2:11]3)[CH2:9]2)=[N:6][CH:7]=1.O1CCOCC1.[NH:32]1[CH:36]=[CH:35][CH:34]=[N:33]1.CN[C@H]1CCCC[C@@H]1NC.C(=O)([O-])[O-].[K+].[K+]>[Cu]I>[OH:22][C@@H:19]1[CH2:20][CH2:21][C@H:16]([N:13]2[CH2:12][CH2:11][C@:10]3([CH2:23][CH2:24][CH2:25][N:8]([C:5]4[N:4]=[CH:3][C:2]([N:32]5[CH:36]=[CH:35][CH:34]=[N:33]5)=[CH:7][N:6]=4)[CH2:9]3)[C:14]2=[O:15])[CH2:17][CH2:18]1

Participants

7

Reactant 5

HCID 1048PyrazoleHCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 13822957(1S,2S)-(+)-N,N'-Dimethylcyclohexane-1,2-diamineHCID 178517861HCID 178517861, compound

Product 1

HCID 178517862HCID 178517862, compound

Reagents, catalysts & solvents 1

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

Conditions

Temperature
150 °C

Procedure

To a solution of (5S)-7-(5-bromopyrimidin-2-yl)-2-(cis-4-hydroxycyclohexyl)-2,7-diazaspiro[4.5]decan-1-one (30 mg, 0.00007 mol, this compound was prepared by using procedures that were analogous to those described for the synthesis of example 420) in 1,4-dioxane (1 mL, 0.01 mol) was added 1H-pyrazole (6.0 mg, 0.0000880 mol), (1S,2S)—N,N′-dimethylcyclohexane-1,2-diamine (2.3 μL, 0.000015 mol), copper(I) iodide (1.4 mg, 0.0000073 mol), and potassium carbonate (0.0213 g, 0.000154 mol). After stirring at 150° C. for 16 h, the reaction mixture was filtered and purified by prep-HPLC to afford the desired product. LC-MS: 397.2 (M+H)+.

Workup

  1. filtrationthe reaction mixture was filtered
  2. custompurified by prep-HPLC

Sources & evidence

ORD record
ord-cad6cdce66184b1dacb03a3ac27873de
Source dataset
uspto-grants-2012_02
Patent number
US08110581B2

Reaction notes

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