Cesium carbonate → HCID 11316843, compound

HRID 2375800Notes

Reaction equation

HRID 2375800 reaction equation
FC(F)(F)C(O)=O.[CH:8]([N:11]1[CH2:16][CH2:15][CH:14]([NH:17][C:18]([C:20]2[NH:21][CH:22]=[C:23]([N+:25]([O-:27])=[O:26])[CH:24]=2)=[O:19])[CH2:13][CH2:12]1)([CH3:10])[CH3:9].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>[CH:8]([N:11]1[CH2:16][CH2:15][CH:14]([NH:17][C:18]([C:20]2[N:21]([CH2:35][C:36](=[O:37])[NH:38][C:39]3[CH:44]=[CH:43][C:42]([Cl:45])=[CH:41][N:40]=3)[CH:22]=[C:23]([N+:25]([O-:27])=[O:26])[CH:24]=2)=[O:19])[CH2:13][CH2:12]1)([CH3:10])[CH3:9]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 34211102-Bromo-N-(5-chloro-2-pyridinyl)acetamideHCID 867607824-Nitro-1h-pyrrole-2-carboxylic acid (1-isopropyl-piperidin-4-yl)-amide trifluoroacetate salt

Product 1

HCID 11316843HCID 11316843, compoundYield 43.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-nitro-1H-pyrrole-2-carboxylic acid (1-isopropyl-piperidin-4-yl)-amide trifluoroacetate salt (30 mg) in DMF (4 mL) was added Cs2CO3 (70 mg). The mixture was stirred for 30 min at RT after which 2-bromo-N-(5-chloro-pyridin-2-yl)-acetamide (27 mg) was added. Stirring was continued for 20 h at RT. The mixture was filtered and directly subjected to preparative HPLC(CH3CN/H2O gradient+0.05% TFA) to give 1-[(5-chloro-pyridin-2-ylcarbamoyl)-methyl]-4-nitro-1H-pyrrole-2-carboxylic acid (1-isopropyl-piperidin-4-yl)-amide (15 mg) as its trifluoroacetate salt. MS (ESI+): m/e=449 [M+H]+, chloro pattern.

Workup

  1. additionwas added
  2. filtrationThe mixture was filtered

Sources & evidence

ORD record
ord-9a59259f77fb40b3949fc1cf936faf20
Source dataset
uspto-grants-2008_12
Patent number
US07465806B2

Reaction notes

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