Succinic anhydride → N-[4-methoxy-3-(3-pyrazin-2-yl-ureido)phenyl]-succinamic acid

HRID 1821727Notes

Reaction equation

HRID 1821727 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([O:18][CH3:19])=[C:6]([NH:8][C:9]([NH:11][C:12]2[CH:17]=[N:16][CH:15]=[CH:14][N:13]=2)=[O:10])[CH:7]=1.[C:20]1(=[O:26])[O:25][C:23](=[O:24])[CH2:22][CH2:21]1>N1C=CC=CC=1>[CH3:19][O:18][C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:20](=[O:26])[CH2:21][CH2:22][C:23]([OH:25])=[O:24])=[CH:7][C:6]=1[NH:8][C:9]([NH:11][C:12]1[CH:17]=[N:16][CH:15]=[CH:14][N:13]=1)=[O:10]

Participants

4

Reactant 2

HCID 7922Succinic anhydrideHCID 220462781-(5-Amino-2-methoxyphenyl)-3-pyrazin-2-yl-urea2×

Product 1

HCID 21034145N-[4-methoxy-3-(3-pyrazin-2-yl-ureido)phenyl]-succinamic acidYield 50%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 1-(5-amino-2-methoxyphenyl)-3-pyrazin-2-yl-urea (Compound 14, Example 4) (260 mg, 1 mmol) and succinic anhydride (131 mg, 1.3 mmol) in dry pyridine (10 mL) was stirred 16 h at room temperature. The resulting solid was collected by filtration and triturated with chloroform, and dried in vacuo to afford the off-white product (175 mg, 50%). 1H NMR (300 Mhz, d6-DMSO) δ: 10.15 (s, 1H), 10.05 (s, 1H), 9.87 (s, 1H), 8.90 (s, 1H), 8.33 (s, 2H), 8.24 (s, 1H), 7.42 (dd, J=8.8, 2.2 Hz, 1H), 6.96 (d, J=8.8 Hz, 1H), 3.87 (s, 3H), 2.54 (br s, 4H).

Workup

  1. filtrationThe resulting solid was collected by filtration
  2. customtriturated with chloroform
  3. customdried in vacuo

Sources & evidence

ORD record
ord-ca809b634e15485c8b4dd018f0f16edb
Source dataset
uspto-grants-2009_10
Patent number
US07608618B2

Reaction notes

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