Triethylamine → HCID 24987658, compound

HRID 1097839Notes

Reaction equation

HRID 1097839 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]([N:13]3[CH2:18][CH2:17][CH:16]([N:19]4[C:27]5[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=5)[CH2:21][C:20]4=[O:28])[CH2:15][CH2:14]3)=[O:12])=[CH:7][NH:8]2)=[CH:4][CH:3]=1.[H-].[Na+].Cl[CH2:32][C:33]([N:35]([CH2:38][CH3:39])[CH2:36][CH3:37])=[O:34].C(N(CC)CC)C>CN(C=O)C>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]([N:13]3[CH2:18][CH2:17][CH:16]([N:19]4[C:27]5[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=5)[CH2:21][C:20]4=[O:28])[CH2:15][CH2:14]3)=[O:12])=[CH:7][N:8]2[CH2:32][C:33]([N:35]([CH2:38][CH3:39])[CH2:36][CH3:37])=[O:34])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 16844Chloro-N,N-diethylacetamideHCID 24758Sodium hydrideHCID 24991356HCID 24991356, compound

Product 1

HCID 24987658HCID 24987658, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1-[1-(6-chloro-1H-indole-3-carbonyl)-piperidin-4-yl]-1,3-dihydroindol-2-one (1 eq) in dry DMF was treated with NaH (1.1 eq) at RT for 15 mins and then a solution of 2-chloro-N,N-diethyl-acetamide (3.3 eq) and triethylamine (3.3 eq) in three portions and the mixture heated to 60° C. for 6 h. Concentration and purification by prep HPLC gave the title compound.

Workup

  1. concentrationConcentration and purification by prep HPLC

Sources & evidence

ORD record
ord-fea06ba1fd4d4e18875f3fd5dc02ccc7
Source dataset
uspto-grants-2012_03
Patent number
US08143281B2

Reaction notes

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