Hydroxyphenylacetic acid → HCID 21105580, compound

HRID 1354693Notes

Reaction equation

HRID 1354693 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=O)=[CH:4][CH:3]=1.O[N:13]1[C:17]2[CH:18]=[CH:19]C=[CH:21][C:16]=2N=N1.Cl.[CH3:23][N:24]([CH3:33])[CH2:25][CH2:26][CH2:27][N:28]=[C:29]=NCC.NC1C=CC(N2CCC(N(C)[C:47](=[O:49])[CH3:48])C2)=CC=1>CN(C=O)C.O>[C:47]([CH2:29][NH:28][CH:27]1[CH2:26][CH2:25][N:24]([C:23]2[CH:21]=[CH:16][C:17]([NH:13][C:9](=[O:11])[CH2:8][C:5]3[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][CH:6]=3)=[CH:18][CH:19]=2)[CH2:33]1)(=[O:49])[CH3:48]

Participants

7

Reactant 4

HCID 127Hydroxyphenylacetic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 21105566N-[1-(4-aminophenyl)pyrrolidin-3-yl]-N-methylacetamide

Product 1

HCID 21105580HCID 21105580, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

4-Hydroxyphenylacetic acid (305 mg), 1-hydroxybenzotriazole (300 mg) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (480 mg) in DMF (5 ml) were stirred with N-[1-(4-aminophenyl)pyrrolidin-3-yl]-N-methylacetamide (470 mg) at room temperature for 3 hours. Water was then added to the mixture, which was extracted with ethyl acetate. The organic phase was washed with saturated sodium chloride solution, dried over sodium sulfate, concentrated and crystallized from diethyl ether. This resulted in the product with the molecular weight of 367.45 (C21H25N3O3); MS (ESI): 368 (M+H+).

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe organic phase was washed with saturated sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customcrystallized from diethyl ether
  6. customThis resulted in the product with the molecular weight of 367.45 (C21H25N3O3)

Sources & evidence

ORD record
ord-debae96f7906478e920e660b8899f706
Source dataset
uspto-grants-2007_05
Patent number
US07223788B2

Reaction notes

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