1,1'-Carbonyldiimidazole → 2-Methoxy-5-[3-(2-methyl-[1,5]-naphthyridin-4-yl)ureido]benzoic Acid Methyl Ester

HRID 1358256Notes

Reaction equation

[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][N:10]=2)[N:5]=[C:4]([CH3:12])[CH:3]=1.[C:13]([N:20]1[CH:24]=[CH:23]N=C1)(N1C=CN=C1)=[O:14].[CH3:25][O:26][C:27](=[O:37])[C:28]1C=C(N)[CH:31]=[CH:30][C:29]=1[O:35][CH3:36]>CN(C=O)C.C(OCC)(=O)C>[CH3:25][O:26][C:27](=[O:37])[C:28]1[CH:23]=[C:24]([NH:20][C:13]([NH:1][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][N:10]=3)[N:5]=[C:4]([CH3:12])[CH:3]=2)=[O:14])[CH:31]=[CH:30][C:29]=1[O:35][CH3:36]

Participants

Conditions

Temperature: 100 °C

Procedure

D2 (0.51 g) was added in portions over 10 min to a solution of 1,1′-carbonyl diimidazole (0.536 g) and 4-N,N-dimethylaminopyridine (0.004 g) in DMF (10 ml). The resulting solution was stirred for 16 h, 5-amino-2-methoxybenzoic acid methyl ester (0.577 g) added in DMF (2 ml) and the mixture heated at 100° C. for 2 h. The mixture was diluted with ethyl acetate and washed with water (×2) and brine, dried (Na2SO4) and solvent removed at reduced pressure. The pale pink solid was triturated with DCM to give the title compound (0.58 g). 1H NMR δ: 2.64 (3H, s), 3.34 (3H, s), 3.81 (3H, s), 7.15 (1H, d), 7.59 (1H, dd), 7.80 (1H, dd), 7.94 (1H, d), 8.29 (1H, dd), 8.34 (1H, s), 8.89 (1H, m), 9.85 (1H, s), 10.05 (1H, s).

Workup

washwashed with water (×2) and brine
dry with materialdried (Na2SO4) and solvent
customremoved at reduced pressure
customThe pale pink solid was triturated with DCM

Sources & evidence

ORD record: ord-1163e3bb3c9e4bd7ab22cefb37e3151e
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06596730B1

Reaction notes

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