Cesium carbonate → HCID 11191911, compound

HRID 2375799Notes

Reaction equation

HRID 2375799 reaction equation
[CH2:1]([O:8][C:9]([C:11]1[NH:12][CH:13]=[C:14]([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: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]([NH:38][C:39]1[CH:44]=[CH:43][C:42]([Cl:45])=[CH:41][N:40]=1)=[O:37]>CN(C=O)C>[CH2:1]([O:8][C:9]([C:11]1[N:12]([CH2:35][C:36](=[O:37])[NH:38][C:39]2[CH:44]=[CH:43][C:42]([Cl:45])=[CH:41][N:40]=2)[CH:13]=[C:14]([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: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 34211102-Bromo-N-(5-chloro-2-pyridinyl)acetamideHCID 69292105HCID 69292105, compound

Product 1

HCID 11191911HCID 11191911, compoundYield 39.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(1-Isopropyl-piperidin-4-ylcarbamoyl)-1H-pyrrole-2-carboxylic acid benzyl ester (50 mg) in DMF (2 mL) was added Cs2CO3 (176 mg), followed by 2-bromo-N-(5-chloro-pyridin-2-yl)-acetamide (34 mg). The mixture was stirred for 20 h at RT whereupon it was filtered. The filtrates were directly subjected to preparative HPLC(CH3CN/H2O gradient+0.05% TFA). Pure 1-[(5-chloro-pyridin-2-ylcarbamoyl)-methyl]-4-(1-isopropyl-piperidin-4-ylcarbamoyl)-1H-pyrrole-2-carboxylic acid benzyl ester (28.5 mg) was obtained as its trifluoroacetate salt. MS (ESI+): m/e=538 [M+H]+, chloro pattern.

Workup

  1. filtrationwas filtered

Sources & evidence

ORD record
ord-81a0f54148c446178d389f5099c29c5f
Source dataset
uspto-grants-2008_12
Patent number
US07465806B2

Reaction notes

Loading…