Glycine → HCID 57513877, compound

HRID 2262730Notes

Reaction equation

HRID 2262730 reaction equation
[CH:1]1([N:5]2[CH2:10][CH2:9][N:8]([C:11](=[O:28])[CH2:12][N:13]3[CH2:18][CH2:17][C:16]4([C:26]5[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=5)[NH:20][C:19]4=[O:27])[CH2:15][CH2:14]3)[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1.Br[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].NCC(O)=O>O1CCOCC1.[Cu]I>[CH:1]1([N:5]2[CH2:10][CH2:9][N:8]([C:11](=[O:28])[CH2:12][N:13]3[CH2:18][CH2:17][C:16]4([C:26]5[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=5)[N:20]([C:30]5[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=5)[C:19]4=[O:27])[CH2:15][CH2:14]3)[CH2:7][CH2:6]2)[CH2:2][CH2:3][CH2:4]1

Participants

7

Reactant 4

HCID 750GlycineHCID 79732-BromopyridineHCID 62657Potassium Phosphate, TribasicHCID 57513875HCID 57513875, compound

Product 1

HCID 57513877HCID 57513877, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 1′-[2-(4-cyclobutylpiperazin-1-yl)-2-oxoethyl]spiro[indole-3,4′-piperidin]-2(1H)-one (0.052 mmol), 2-bromopyridine (0.078 mmol), CuI (2 mg, 0.01 mmol), K3PO4 (28 mg, 0.13 mmol), glycine (1 mg, 0.012 mmol) in 1,4-dioxane (3 ml) is degassed by Argon then heated in a sealed tube at 110° C. for 24 h. Solid is filtered and the filtrate is concentrated and purified by PTLC to give the title compound as a light yellow solid. LC-MS (M+1): 459.3.

Workup

  1. customis degassed by Argon
  2. filtrationSolid is filtered
  3. concentrationthe filtrate is concentrated
  4. custompurified by PTLC

Sources & evidence

ORD record
ord-74fcd2bdc2214f748280201d41f6bba7
Source dataset
uspto-grants-2010_12
Patent number
US07851474B2

Reaction notes

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