4-Formylbenzoic acid → HCID 24938105, compound

HRID 391642Notes

Reaction equation

HRID 391642 reaction equation
[C:1]([C:4]1[N:12]=[C:11]([C:13]2[CH:21]=[CH:20][C:16]([C:17]([OH:19])=[O:18])=[CH:15][CH:14]=2)[N:10]=[C:9]2[C:5]=1[NH:6][C:7](=[O:30])[N:8]2[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[O:28][CH3:29])(=[O:3])[NH2:2].N/[C:32](/C#N)=C(\NC(NC1C=CC=CC=1OC)=O)/C#N.C(C1C=CC(C(O)=O)=CC=1)=O>C(N(CC)CC)C>[CH3:32][O:18][C:17](=[O:19])[C:16]1[CH:15]=[CH:14][C:13]([C:11]2[N:10]=[C:9]3[C:5]([NH:6][C:7](=[O:30])[N:8]3[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[O:28][CH3:29])=[C:4]([C:1](=[O:3])[NH2:2])[N:12]=2)=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 120884-Formylbenzoic acidHCID 24938231HCID 24938231, compoundHCID 57474547HCID 57474547, compound

Product 1

HCID 24938105HCID 24938105, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

4-[6-Carbamoyl-9-(2-methoxy-phenyl)-8-oxo-8,9-dihydro-7H-purin-2-yl]-benzoic acid. (Z)-1-(2-Amino-1,2-dicyanovinyl)-3-(2-methoxyphenyl)urea (See Example 2.A) (0.30 g, 1.2 mmol), 4-formylbenzoic acid (0.44 g, 2.65 mmol) and triethylamine (3.0 mL) were reacted according to General Procedure B. The crude residue was purified using Biotage silica gel chromatography (0-100% ethyl acetate in hexanes) to afford the title compound in 99.4% purity (0.129 g, 0.069 mmol, 51% yield). 1H NMR (300 MHz, DMSO-d6) δ 11.85 (s, 1H), 8.56 (s, 1H), 8.48 (d, J=8.2, 1H), 8.03 (s, 1H), 7.99 (d, J=8.5, 1H), 7.49-7.61 (m, 1H), 7.31 (d, J=8.5, 1H), 7.17 (td, J=7.7, 1.1, 1H), 3.76 (s, 1H); MS (ESI) m/z 420.1 [M+1]+; mp 328-332° C.

Workup

  1. customThe crude residue was purified

Sources & evidence

ORD record
ord-5058bbc3b26940cc9b581dc317418fa7
Source dataset
uspto-grants-2013_02
Patent number
US08383634B2

Reaction notes

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