N-Hydroxysuccinimide → HCID 17921840, compound

HRID 326718Notes

Reaction equation

HRID 326718 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=[CH:8][C:9]([OH:11])=[O:10])[CH:2]=1.O[N:13]1[C:17](=[O:18])[CH2:16][CH2:15][C:14]1=[O:19].CCN=C=NCCCN(C)C.Cl>C(Cl)Cl.CN(C=O)C>[CH2:16]1[C:17](=[O:18])[N:13]([O:10][C:9](/[CH:8]=[CH:7]/[C:3]2[CH:4]=[CH:5][CH:6]=[N:1][CH:2]=2)=[O:11])[C:14](=[O:19])[CH2:15]1

Participants

6

Reactant 3

HCID 80170N-HydroxysuccinimideHCID 1019843-(3-Pyridinyl)-2-propenoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 17921840HCID 17921840, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 3-(3-pyridyl)acrylic acid (500 mg: commercially available from Aldrich Chemical Company), N-hydroxysuccinimide (463 mg), and EDCl (707 mg) in methylene chloride (20 mL) and DMF (10 mL) was stirred at ambient temperature for 18 hours. The product was isolated as described in Example 3a to yield 740 mg of the title compound as a white solid. MS (Cl/NH3) m/e 247 (M+H)+. 1H NMR(CDCl3, 300 MHz) δ2.87 (br s,4H), 7.15 (d,J=16 Hz,1H), 7.48-7.53 (m,1H), 8.02 (d,1H), 8.31 (dt,J=9 Hz,1H), 8.66 (dd,J=6 Hz,1H), 8.99 (d,J=2 Hz,1H).

Workup

  1. customThe product was isolated

Sources & evidence

ORD record
ord-e6757b0d73aa4c60add2f432af649b97
Source dataset
uspto-grants-1993_12
Patent number
US05270302

Reaction notes

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