Cesium carbonate → 1-[5-(5-chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-5-phenyl-1H-pyrrole-2-carboxylic acid (1-isopropyl-piperidin-4-yl)-amide

HRID 2375804Notes

Reaction equation

HRID 2375804 reaction equation
[CH:1]([N:4]1[CH2:9][CH2:8][CH:7]([NH:10][C:11]([C:13]2[NH:14][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:16][CH:17]=2)=[O:12])[CH2:6][CH2:5]1)([CH3:3])[CH3:2].C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:31][C:32]1[CH:36]=[C:35]([C:37]2[S:38][C:39]([Cl:42])=[CH:40][CH:41]=2)[O:34][N:33]=1>CN(C=O)C>[CH:1]([N:4]1[CH2:5][CH2:6][CH:7]([NH:10][C:11]([C:13]2[N:14]([CH2:31][C:32]3[CH:36]=[C:35]([C:37]4[S:38][C:39]([Cl:42])=[CH:40][CH:41]=4)[O:34][N:33]=3)[C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:16][CH:17]=2)=[O:12])[CH2:8][CH2:9]1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 111501463-Bromomethyl-5-(5-chloro-thiophen-2-yl)-isoxazoleHCID 866110375-phenyl-1H-pyrrole-2-carboxylic acid (1-isopropyl-piperidin-4-yl)-amide

Product 1

HCID 113756341-[5-(5-chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-5-phenyl-1H-pyrrole-2-carboxylic acid (1-isopropyl-piperidin-4-yl)-amideYield 18.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-phenyl-1H-pyrrole-2-carboxylic acid (1-isopropyl-piperidin-4-yl)-amide (50 mg) in DMF (2 mL) was added Cs2CO3 (105 mg). The mixture was stirred for 30 min at RT. 3-Bromomethyl-5-(5-chloro-thiophen-2-yl)-isoxazole (45 mg) was added and stirring was continued for 3 h at RT. The mixture was filtered and directly subjected to preparative HPLC(CH3CN/H2O gradient+0.05% TFA) to give 1-[5-(5-chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-5-phenyl-1H-pyrrole-2-carboxylic acid (1-isopropyl-piperidin-4-yl)-amide (15 mg) as its trifluoroacetate salt. MS (ESI+): m/e=509 [M+H]+, chloro pattern.

Workup

  1. stirringstirring
  2. waitwas continued for 3 h at RT
  3. filtrationThe mixture was filtered

Sources & evidence

ORD record
ord-371da35aadfb45ba868d99b49b98daec
Source dataset
uspto-grants-2008_12
Patent number
US07465806B2

Reaction notes

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