Ammonia → N6,N6-bis(4-methoxybenzyl)-2,7-naphthyridine-1,6-diamine

HRID 874690Notes

Reaction equation

HRID 874690 reaction equation
[CH3:1][O:2][C:3]1[CH:32]=[CH:31][C:6]([CH2:7][N:8]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)[C:9]2[CH:16]=[C:15](/[CH:17]=[CH:18]/[N:19](C)C)[C:12]([C:13]#[N:14])=[CH:11][N:10]=2)=[CH:5][CH:4]=1.N>O1CCOCC1>[CH3:30][O:29][C:26]1[CH:25]=[CH:24][C:23]([CH2:22][N:8]([CH2:7][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:32][CH:31]=2)[C:9]2[CH:16]=[C:15]3[C:12](=[CH:11][N:10]=2)[C:13]([NH2:14])=[N:19][CH:18]=[CH:17]3)=[CH:28][CH:27]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 89525377(E)-6-(bis(4-methoxybenzyl)amino)-4-(2-(dimethylamino)vinyl)nicotinonitrile

Product 1

HCID 117672701N6,N6-bis(4-methoxybenzyl)-2,7-naphthyridine-1,6-diamine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of crude 4-4 (9.40 g, <19.3 mmol), ammonia (7 M in methanol; 150 mL, 1050 mmol), and 1,4-dioxane (50.0 mL) was placed in a 350 mL sealed tube. The resulting mixture was stirred at 90° C. for 138 hours and cooled to ambient temperature. The reaction mixture was concentrated under reduced pressure to give 10.9 g of 4-5 as a brown oil. The crude product was used for next step without further purification.

Workup

  1. customsealed tube
  2. temperaturecooled to ambient temperature
  3. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a97027bf7b8e4554b55e7eccbd20e5c2
Source dataset
uspto-grants-2015_03
Patent number
US08980916B2

Reaction notes

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