1-[4-amino-7-bromo-2-(ethoxymethyl)-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl]-2-methylpropan-2-ol → Tert-butyl 2-[(3-amino-7-bromo[1,5]naphthyridin-4-yl)amino]-1,1-dimethylethylcarbamate

HRID 598039Notes

Reaction equation

HRID 598039 reaction equation
NC1C2N=C(COCC)N(CC(C)(O)C)C=2C2N=CC(Br)=CC=2N=1.[Br:25][C:26]1[CH:35]=[C:34]2[C:29]([C:30]([NH:39][CH2:40][C:41]([NH:44][C:45](=[O:51])[O:46][C:47]([CH3:50])([CH3:49])[CH3:48])([CH3:43])[CH3:42])=[C:31]([N+:36]([O-])=O)[CH:32]=[N:33]2)=[N:28][CH:27]=1>C(#N)C>[NH2:36][C:31]1[CH:32]=[N:33][C:34]2[C:29]([C:30]=1[NH:39][CH2:40][C:41]([NH:44][C:45](=[O:51])[O:46][C:47]([CH3:50])([CH3:49])[CH3:48])([CH3:43])[CH3:42])=[N:28][CH:27]=[C:26]([Br:25])[CH:35]=2

Participants

4

Reactant 2

HCID 589706811-[4-amino-7-bromo-2-(ethoxymethyl)-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl]-2-methylpropan-2-olHCID 67052497Tert-butyl 2-[(7-bromo-3-nitro[1,5]naphthyridin-4-yl)amino]-1,1-dimethylethylcarbamate

Product 1

HCID 67052529Tert-butyl 2-[(3-amino-7-bromo[1,5]naphthyridin-4-yl)amino]-1,1-dimethylethylcarbamateYield 99.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A modification of the method described in Part B of the preparation of 1-[4-amino-7-bromo-2-(ethoxymethyl)-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl]-2-methylpropan-2-ol was used to reduce tert-butyl 2-[(7-bromo-3-nitro[1,5]naphthyridin-4-yl)amino]-1,1-dimethylethylcarbamate (138.0 g, 313.4 mmol). The reaction was placed under hydrogen pressure for 5.5 hours. The reaction yielded 128 g of tert-butyl 2-[(3-amino-7-bromo[1,5]naphthyridin-4-yl)amino]-1,1-dimethylethylcarbamate containing some acetonitrile.

Workup

  1. customfor 5.5 hours

Sources & evidence

ORD record
ord-d971c751401c470a8283e6e9f753ca6d
Source dataset
uspto-grants-2011_03
Patent number
US07897609B2

Reaction notes

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