Triethylamine → HCID 23020436, compound

HRID 747178Notes

Reaction equation

HRID 747178 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[O:9][CH:10]=[CH:11][CH:12]=2)[C:5]([C:13]2[CH:18]=[CH:17][N:16]([CH2:19][C:20]([OH:22])=O)[C:15](=[O:23])[CH:14]=2)=[CH:4][N:3]=1.ON1C2C=CC=CC=2N=N1.CN(C)CCCN=C=NCC.Cl.[CH2:46]([NH:48][CH2:49][CH3:50])[CH3:47].C(N(CC)CC)C>CN(C)C=O.O>[CH2:46]([N:48]([CH2:49][CH3:50])[C:20](=[O:22])[CH2:19][N:16]1[CH:17]=[CH:18][C:13]([C:5]2[C:6]([C:8]3[O:9][CH:10]=[CH:11][CH:12]=3)=[N:7][C:2]([NH2:1])=[N:3][CH:4]=2)=[CH:14][C:15]1=[O:23])[CH3:47]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 10197650Diethylammonium chlorideHCID 59749123HCID 59749123, compound

Product 1

HCID 23020436HCID 23020436, compoundYield 6.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A suspension of {4-[2-amino-4-(2-furyl)-5-pyrimidinyl]-2-oxo-1,2-dihydro-1-pyridinyl}acetic acid (10 mg, 32 μmol), 1-hydroxybenzotriazole (15 mg, 98 μmol), 3-(3′-dimethylaminopropyl)-1-ethylcarbodiimide (15 mg, 96 μmol), diethylamine hydrochloride (18 mg, 164 μmol) and triethylamine (22 μl, 160 μmol) in N,N-dimethylformamide (1.0 ml) was stirred at room temperature for 17 hours. The reaction mixture was diluted with water and then extracted with ethyl acetate. The organic layer was concentrated and then purified by HPLC, to give the title compound (0.73 mg, 6%).

Workup

  1. extractionextracted with ethyl acetate
  2. concentrationThe organic layer was concentrated
  3. custompurified by HPLC

Sources & evidence

ORD record
ord-1da8b26b29dd4a90a75b56ffddfba487
Source dataset
uspto-grants-2008_07
Patent number
US07396836B2

Reaction notes

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