3-Pyrroline → HCID 136354828, compound

HRID 2249525Notes

Reaction equation

HRID 2249525 reaction equation
[NH2:1][C:2]1[N:3]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[C:16]=2[Cl:22])[C:4]([C:7]2[CH:8]=[C:9]([C:12](O)=[O:13])[NH:10][CH:11]=2)=[N:5][N:6]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.[NH:35]1[CH2:39][CH:38]=[CH:37][CH2:36]1>CC(N(C)C)=O>[NH2:1][C:2]1[N:3]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[C:16]=2[Cl:22])[C:4]([C:7]2[CH:8]=[C:9]([C:12]([N:35]3[CH2:39][CH:38]=[CH:37][CH2:36]3)=[O:13])[NH:10][CH:11]=2)=[N:5][N:6]=1

Participants

5

Reactant 3

HCID 660593-PyrrolineHCID 682631,1'-CarbonyldiimidazoleHCID 136354821HCID 136354821, compound

Product 1

HCID 136354828HCID 136354828, compoundYield 64.2%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a solution of 4-[5-amino-4-(2,3-dichloro-phenyl)-4H-[1,2,4]triazol-3-yl]-1H-pyrrole-2-carboxylic acid (10 mg, 0.03 mmol) in DMA (1 mL) was added CDI (6 mg, 0.04 mmol). The solution was stirred at RT for 30 min before the addition of 2,5-dihydro-1H-pyrrole (6 mg, 0.09 mmol). The reaction mixture was stirred at RT for another 60 min and purified by Gilson HPLC directly to afford a white solid (7.5 mg, 64%). MS (ES+): m/e=389.2 (M+H); LC: 2.65 min.

Workup

  1. custompurified by Gilson HPLC directly

Sources & evidence

ORD record
ord-4a5369aa68854e8393fd78ace7e559e0
Source dataset
uspto-grants-2008_01
Patent number
US07314885B2

Reaction notes

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