Triethylamine → 1-(3-Acetyl-4-methoxyphenyl)-3-(2-methyl-[1,5]-naphthyridin-4-yl)urea

HRID 1358258Notes

Reaction equation

HRID 1358258 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[O:13][CH3:14])C(O)=O)(=[O:3])[CH3:2].C([N:17]([CH2:20]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:29])C=CC=CC=1.[NH2:39][C:40]1[C:49]2[C:44](=[CH:45][CH:46]=[CH:47][N:48]=2)[N:43]=[C:42]([CH3:50])[CH:41]=1>C1(C)C=CC=CC=1>[C:1]([C:4]1[CH:5]=[C:6]([NH:17][C:20]([NH:39][C:40]2[C:49]3[C:44](=[CH:45][CH:46]=[CH:47][N:48]=3)[N:43]=[C:42]([CH3:50])[CH:41]=2)=[O:29])[CH:10]=[CH:11][C:12]=1[O:13][CH3:14])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 112866094-Amino-2-methyl-[1,5]-naphthyridineHCID 181844503-Acetyl-4-methoxybenzoic acid

Product 1

HCID 98847681-(3-Acetyl-4-methoxyphenyl)-3-(2-methyl-[1,5]-naphthyridin-4-yl)urea

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3-Acetyl-4-methoxybenzoic acid (0.082 g) in toluene (4 ml) was treated with triethylamine (0.176 ml) and subsequently with diphenylphosphoryl azide (0.092 ml). The mixture was stirred for 16 h at room temperature, D2 (0.067 g) added and the mixture heated to reflux for 4 h. After cooling to room temperature solvent was removed at reduced pressure and the residue column chromatographed (silica gel, 0-10% methanol in DCM containing 1% ammonia) to give the title compound (0.03 g) as a colourless solid. H NMR δ: 2.55 (3H, s), 2.63 (3H, s), 3.89 (3H, s), 7.18 (1H, d), 7.68 (1H, dd), 7.77-7.83 (2H, m), 8.28 (1H, dd), 8.34 (1H, s), 8.89 (1H, m), 9.85 (1H, s), 10.03 (1H, s). m/z (API+): 351 (MH+).

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux for 4 h
  3. temperatureAfter cooling to room temperature solvent
  4. customwas removed at reduced pressure
  5. customthe residue column chromatographed (silica gel, 0-10% methanol in DCM containing 1% ammonia)

Sources & evidence

ORD record
ord-9248aec9200f4856a0bc70a29be7091f
Source dataset
uspto-grants-2003_07
Patent number
US06596730B1

Reaction notes

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