Potassium Carbonate → tert-butyl {2-[7-bromo-2-(ethoxymethyl)-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl]-1,1-dimethylethyl}carbamate

HRID 598041Notes

Reaction equation

HRID 598041 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:43][CH2:44][C:45]([NH:48][C:49](=[O:55])[O:50][C:51]([CH3:54])([CH3:53])[CH3:52])([CH3:47])[CH3:46])=[C:31]([NH:36][C:37](=O)[CH2:38][O:39][CH2:40][CH3:41])[CH:32]=[N:33]2)=[N:28][CH:27]=1.C(=O)([O-])[O-].[K+].[K+]>>[Br:25][C:26]1[CH:27]=[N:28][C:29]2[C:30]3[N:43]([CH2:44][C:45]([NH:48][C:49](=[O:55])[O:50][C:51]([CH3:52])([CH3:53])[CH3:54])([CH3:46])[CH3:47])[C:37]([CH2:38][O:39][CH2:40][CH3:41])=[N:36][C:31]=3[CH:32]=[N:33][C:34]=2[CH:35]=1

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 589706811-[4-amino-7-bromo-2-(ethoxymethyl)-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl]-2-methylpropan-2-olHCID 67052411Tert-butyl 2-({7-bromo-3-[(ethoxyacetyl)amino][1,5]naphthyridin-4-yl}amino)-1,1-dimethylethylcarbamate

Product 1

HCID 86615171tert-butyl {2-[7-bromo-2-(ethoxymethyl)-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl]-1,1-dimethylethyl}carbamateYield 102.5%

Procedure

A modification of the method described in Part D 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 treat tert-butyl 2-({7-bromo-3-[(ethoxyacetyl)amino][1,5]naphthyridin-4-yl}amino)-1,1-dimethylethylcarbamate (55.6 g, 0.104 mol) with potassium carbonate (55.6 g). After the ethanol was removed under reduced pressure, and the resulting mixture was extracted with dichloromethane (4×300 mL). The combined extracts were concentrated under reduced pressure to provide 51 g of tert-butyl {2-[7-bromo-2-(ethoxymethyl)-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl]-1,1-dimethylethyl}carbamate as a yellowish brown solid.

Workup

  1. customAfter the ethanol was removed under reduced pressure
  2. extractionthe resulting mixture was extracted with dichloromethane (4×300 mL)
  3. concentrationThe combined extracts were concentrated under reduced pressure

Sources & evidence

ORD record
ord-a3216c0182ed438c9088e47de6f1fa46
Source dataset
uspto-grants-2011_03
Patent number
US07897609B2

Reaction notes

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