Cesium carbonate → HCID 69289215, compound

HRID 2375797Notes

Reaction equation

HRID 2375797 reaction equation
[CH2:1]([O:8][C:9]([C:11]1[NH:12][C:13]([C:16](=[O:27])[NH:17][CH:18]2[CH2:23][CH2:22][N:21]([CH:24]([CH3:26])[CH3:25])[CH2:20][CH2:19]2)=[CH:14][CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:35][C:36]1[CH:40]=[C:39]([C:41]2[S:42][C:43]([Cl:46])=[CH:44][CH:45]=2)[O:38][N:37]=1>CN(C=O)C>[CH2:1]([O:8][C:9]([C:11]1[N:12]([CH2:35][C:36]2[CH:40]=[C:39]([C:41]3[S:42][C:43]([Cl:46])=[CH:44][CH:45]=3)[O:38][N:37]=2)[C:13]([C:16](=[O:27])[NH:17][CH:18]2[CH2:23][CH2:22][N:21]([CH:24]([CH3:25])[CH3:26])[CH2:20][CH2:19]2)=[CH:14][CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 111501463-Bromomethyl-5-(5-chloro-thiophen-2-yl)-isoxazoleHCID 69289819HCID 69289819, compound

Product 1

HCID 69289215HCID 69289215, compoundYield 49.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-(1-isopropyl-piperidin-4-ylcarbamoyl)-1H-pyrrole-2-carboxylic acid benzyl ester (20 mg) in DMF (1 mL) was added Cs2CO3 μl mg). The mixture was stirred for 30 min at RT. 3-Bromomethyl-5-(5-chloro-thiophen-2-yl)-isoxazole (15 mg) was added and stirring was continued for 20 h at RT whereupon the mixture was filtered. The filtrate was directly subjected to preparative HPLC(CH3CN/H2O gradient+0.05% TFA). Pure 1-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-5-(1-isopropyl-piperidin-4-ylcarbamoyl)-1H-pyrrol e-2-carboxylic acid benzyl ester (15 mg) was obtained as its trifluoroacetate salt. MS (ESI+): m/e=567 [M+H]+, chloro pattern.

Workup

  1. stirringstirring
  2. waitwas continued for 20 h at RT whereupon the mixture
  3. filtrationwas filtered

Sources & evidence

ORD record
ord-d23573fb17044094af26a62195eacecd
Source dataset
uspto-grants-2008_12
Patent number
US07465806B2

Reaction notes

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