Water → 1,6-Naphthyridin-2(1H)-One

HRID 1257139Notes

Reaction equation

HRID 1257139 reaction equation
C[O:2][C:3]1[CH:11]=[CH:10][C:6]([CH2:7][NH:8][CH3:9])=[CH:5][CH:4]=1.C1CCN2C(=[N:16]CCC2)CC1.O>CN1C(=O)CCC1>[NH:16]1[C:5]2[C:6](=[CH:7][N:8]=[CH:9][CH:4]=2)[CH:10]=[CH:11][C:3]1=[O:2]

Participants

5

Reactant 3

HCID 962WaterHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 4854071-(4-methoxyphenyl)-N-methylmethanamine

Product 1

HCID 5896741,6-Naphthyridin-2(1H)-OneYield 173.7%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of Example A18 (22 g, 65.7 mmol), (4-methoxy-benzyl)-methyl-amine (14.9 g, 98.5 mmol) and DBU (15 g, 98.5 mmol) in NMP (120 mL) was heated at 160° C. for 5 h. The mixture was poured into 200 mL of water while stirring and the resulting solids were collected by filtration, washed with water, dried and then washed with Et2O to give 3-(5-amino-2,4-difluoro-phenyl)-1-ethyl-7-[4-methoxy-benzyl)-methyl-amino]-1H-[1,6]naphthyridin-2-one (25 g, yield 85% yield). 1H NMR (300 MHz, DMSO-d6): δ 8.51 (s, 1H), 7.80 (s, 1H), 7.19-7.17 (d, J=8.7 Hz, 2H), 7.06 (t, J=10.2 Hz, 1H), 6.90-6.81 (m, 3H), 6.32 (s, 1H), 5.02 (s, 2H), 4.86 (s, 2H), 4.19 (q, J=6.9 Hz, 2H), 3.72 (s, 3H), 3.14 (s, 3H), 1.14 (t, J=6.9 Hz, 3H); MS (ESI): m/z 451.1 [M+H]+.

Workup

  1. customwas heated at 160° C. for 5 h
  2. filtrationthe resulting solids were collected by filtration
  3. washwashed with water
  4. customdried
  5. washwashed with Et2O

Sources & evidence

ORD record
ord-a04ea4b5dd9e489fbaae48684e4a1907
Source dataset
uspto-grants-2013_06
Patent number
US08461179B1

Reaction notes

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