Dimethylformamide → HCID 9951306, compound

HRID 1265043Notes

Reaction equation

HRID 1265043 reaction equation
[O:1]=[C:2]1[NH:6][C:5](=[O:7])[CH:4]([CH2:8][C:9]2[CH:10]=[CH:11][C:12]([O:18][CH3:19])=[C:13]([CH:17]=2)[C:14]([OH:16])=O)[S:3]1.[N:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH2:26][NH2:27].Cl.CN(C)CCCN=C=NCC.CN(C)C=O>O>[N:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH2:26][NH:27][C:14](=[O:16])[C:13]1[CH:17]=[C:9]([CH2:8][CH:4]2[S:3][C:2](=[O:1])[NH:6][C:5]2=[O:7])[CH:10]=[CH:11][C:12]=1[O:18][CH3:19]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 195092-PyridinemethanamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 9943613HCID 9943613, compound

Product 1

HCID 9951306HCID 9951306, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5-[(2,4-Dioxothiazolidin-5-yl)methyl]-2-methoxybenzoic acid (282 mg, 1.00 mmol), 2-picolylamine (114 mg, 1.05 mmol), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (230 mg, 1.20 mmol) and N,N-dimethylformamide (5 mL) were mixed and stirred for 5.5 hours at room temperature, which was then allowed to stand overnight. After water was added to the reaction mixture, this was made acidic and extracted with ethyl acetate. The extracted solution was dried and then concentrated. The residue was recrystallized from acetonitrile to obtain 73.7 mg (20%) of the title compound as colorless crystals.

Workup

  1. waitto stand overnight
  2. extractionextracted with ethyl acetate
  3. customThe extracted solution was dried
  4. concentrationconcentrated
  5. customThe residue was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-beea16d6ea6d467d8c4e3251ca736dc0
Source dataset
uspto-grants-2003_04
Patent number
US06545026B1

Reaction notes

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