Cesium carbonate → HCID 11442917, compound

HRID 130658Notes

Reaction equation

HRID 130658 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[C:5]2[O:12][C:13]1[CH:26]=[CH:25][C:16]2[C:17]([C:21]([NH:23][CH3:24])=[O:22])=[C:18]([CH3:20])[S:19][C:15]=2[CH:14]=1.Br[CH2:28][CH2:29][CH:30]1[CH2:34][CH2:33][CH2:32][N:31]1[CH3:35].C([O-])([O-])=O.[Cs+].[Cs+]>CS(C)=O>[CH3:24][NH:23][C:21]([C:17]1[C:16]2[CH:25]=[CH:26][C:13]([O:12][C:5]3[C:4]4[C:9](=[CH:10][CH:11]=[C:2]([O:1][CH2:28][CH2:29][CH:30]5[CH2:34][CH2:33][CH2:32][N:31]5[CH3:35])[CH:3]=4)[N:8]=[CH:7][CH:6]=3)=[CH:14][C:15]=2[S:19][C:18]=1[CH3:20])=[O:22]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 11740028HCID 11740028, compoundHCID 597307442-(2-Bromoethyl)-1-methylpyrrolidine

Product 1

HCID 11442917HCID 11442917, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 25-F (70 mg, 0.19 mmol), 2-(2-bromoethyl)-1-methylpyrrolidine 25-B (110 mg crude and Cs2CO3 (94 mg, 1.5 mmol) in DMSO (2 ml) was heated to 120° C. for 2 hours. The title compound, N,2-dimethyl-6-({6-[2-(1-methylpyrrolidin-2-yl)ethoxy]quinolin-4-yl}oxy)-1-benzothiophene-3-carboxamide 25 (21 mg) was isolated by HPLC (Dionex System) using 20-60% CH3CN/H2O (0.1% AcOH) over 30 minutes.

Sources & evidence

ORD record
ord-2105e93169af421db107b88cd7e43b29
Source dataset
uspto-grants-2008_06
Patent number
US07381824B2

Reaction notes

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