Triethylamine → HCID 24809796, compound

HRID 1446152Notes

Reaction equation

HRID 1446152 reaction equation
[C:1]1([C:7]2[O:11][N:10]=[CH:9][C:8]=2[C:12]([OH:14])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.C(N=C=NCCCN(C)C)C.C(N(CC)CC)C.Cl.[CH3:35][N:36]([CH3:50])[C:37]([C:39]1([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[CH2:43][CH2:42][NH:41][CH2:40]1)=[O:38]>ClCCl>[CH3:35][N:36]([CH3:50])[C:37]([C:39]1([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[CH2:43][CH2:42][N:41]([C:12]([C:8]2[CH:9]=[N:10][O:11][C:7]=2[C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[O:14])[CH2:40]1)=[O:38]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 147872535-Phenylisoxazole-4-carboxylic acidHCID 68685778HCID 68685778, compound

Product 1

HCID 24809796HCID 24809796, compoundYield 17.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-phenylisoxazol-4-carboxylic acid (15 mg, 0.08 mmol) in dichloromethane (2 mL) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC) (15 mg, 0.08 mol), triethylamine (33 μL, 0.24 mmol) and finally N,N-dimethyl-3-phenylpyrrolidine-3-carboxamide hydrochloride (15 mg, 0.06 mmol) and allowed to stir at ambient temperature overnight. The residue was purified using straight phaseHPLC (1:1 hexane/ethyl acetate) to afford the title compound (4 mg). HRMS (ESI, pos. ion) m/z calcd for C23H23N3O3: 389.1739, found 389.1744.

Workup

  1. customThe residue was purified

Sources & evidence

ORD record
ord-46679dffdaad452e97ddbba4e37d5740
Source dataset
uspto-grants-2010_02
Patent number
US07666888B2

Reaction notes

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