O-Methyltyramine → HCID 69299539, compound

HRID 1930320Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:22])=[C:6]([C:8]2[C:9](=[O:21])[N:10]([CH2:19][CH3:20])[C:11]3[C:16]([CH:17]=2)=[CH:15][N:14]=[C:13](Cl)[CH:12]=3)[CH:7]=1.COC1C=CC(C[CH2:30][NH2:31])=CC=1.C1CCN2C(=NCCC2)CC1.FC(F)(F)C(O)=O>>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:22])=[C:6]([C:8]2[C:9](=[O:21])[N:10]([CH2:19][CH3:20])[C:11]3[C:16]([CH:17]=2)=[CH:15][N:14]=[C:13]([NH:31][CH3:30])[CH:12]=3)[CH:7]=1

Participants

Reactant 4

HCID 4657O-Methyltyramine

HCID 6422Trifluoroacetic acid

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

HCID 86620164HCID 86620164, compound

Product 1

HCID 69299539HCID 69299539, compoundYield 43%

Procedure

Using a procedure analogous to Example A26, 3-(5-amino-2-methylphenyl)-7-chloro-1-ethyl-1,6-naphthyridin-2(1H)-one (1.9 g, 6.4 mmol), 4-methoxybenzylmethylamine (1.5 g, 9.6 mmol), DBU (1.6 g, 9.6 mmol), and trifluoroacetic acid (10 mL, 134 mmol) were combined to give 3-(5-amino-2-methylphenyl)-1-ethyl-7-(methylamino)-1,6-naphthyridin-2(1H)-one (0.84 g, 43% yield, 2 steps). 1H NMR (300 MHz, DMSO-d6): δ 8.36 (s, 1 H), 7.56 (s, 1 H), 6.91-6.82 (m, 2 H), 6.47-6.39 (m, 2 H), 6.22 (s, 1 H), 4.80 (s, 2 H), 4.13 (q, J=6.9 Hz, 2 H), 2.84 (d, J=4.8 Hz, 3 H), 1.92 (s, 3 H), 1.19 (t, J=6.9 Hz, 3 H); MS (ESI) m/z: 308.9 [M+H]+.

Sources & evidence

ORD record: ord-6217e2bdd0f8484284d20de74c18fab1
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188113B2

Reaction notes

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