1-(4-methoxyphenyl)-N-methylmethanamine → HCID 69296325, compound

HRID 1930293Notes

Reaction equation

HRID 1930293 reaction equation
[NH2:1][C:2]1[C:3]([F:22])=[CH:4][C:5]([Cl:21])=[C:6]([C:8]2[C:9](=[O:20])[N:10]([CH3:19])[C:11]3[C:16]([CH:17]=2)=[CH:15][N:14]=[C:13](Cl)[CH:12]=3)[CH:7]=1.[CH3:23][O:24][C:25]1[CH:33]=[CH:32][C:28]([CH2:29][NH:30][CH3:31])=[CH:27][CH:26]=1>CCOCC>[CH3:23][O:24][C:25]1[CH:33]=[CH:32][C:28]([CH2:29][N:30]([CH3:31])[C:13]2[CH:12]=[C:11]3[C:16]([CH:17]=[C:8]([C:6]4[CH:7]=[C:2]([NH2:1])[C:3]([F:22])=[CH:4][C:5]=4[Cl:21])[C:9](=[O:20])[N:10]3[CH3:19])=[CH:15][N:14]=2)=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 4854071-(4-methoxyphenyl)-N-methylmethanamineHCID 86620157HCID 86620157, compound

Product 1

HCID 69296325HCID 69296325, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 3-(5-amino-2-chloro-4-fluorophenyl)-7-chloro-1-methyl-1,6-naphthyridin-2(1H)-one (2.5 g, 7.4 mmol) and 4-methoxy-N-methylbenzylamine (4 mL) was heated to 180° C. under N2 for about 3 hour. After cooling, the reaction mixture was diluted with Et2O. The precipitate was filtered, washed with water, and dried to give 7-((4-methoxybenzyl)(methyl)amino)-3-(5-amino-2-chloro-4-fluorophenyl)-1-methyl-1,6-naphthyridin-2(1H)-one (3 g, 89% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.47 (s, 1 H), 7.77 (s, 1 H) 7.22 (m, 2 H), 7.17 (d, J=8.0 Hz, 2 H), 6.86 (d, J=8.4 Hz, 2 H), 5.86 (d, J=9.6 Hz, 1H), 6.30 (s, 1 H), 5.32 (s, 2 H) 4.87 (s, 1 H), 3.72 (s, 3 H), 3.52 (s, 3 H), 3.09 (s, 3 H); MS (ESI) m/z: 453.2[M+H]+.

Workup

  1. temperatureAfter cooling
  2. filtrationThe precipitate was filtered
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-248411a7de594075bc0cc7c9ad693e9e
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

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