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Ethoxyacetyl chloride → Tert-butyl 2-({7-bromo-3-[(ethoxyacetyl)amino][1,5]naphthyridin-4-yl}amino)-1,1-dimethylethylcarbamate hydrochloride

HRID 598040
Notes
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Reaction equation

HRID 598040 reaction equation
NC1C2N=C(COCC)N(CC(C)(O)C)C=2C2N=CC(Br)=CC=2N=1.[NH2:25][C:26]1[CH:27]=[N:28][C:29]2[C:34]([C:35]=1[NH:36][CH2:37][C:38]([NH:41][C:42](=[O:48])[O:43][C:44]([CH3:47])([CH3:46])[CH3:45])([CH3:40])[CH3:39])=[N:33][CH:32]=[C:31]([Br:49])[CH:30]=2.[CH2:50]([O:52][CH2:53][C:54]([Cl:56])=[O:55])[CH3:51]>C(#N)C>[ClH:56].[Br:49][C:31]1[CH:30]=[C:29]2[C:34]([C:35]([NH:36][CH2:37][C:38]([NH:41][C:42](=[O:48])[O:43][C:44]([CH3:47])([CH3:46])[CH3:45])([CH3:40])[CH3:39])=[C:26]([NH:25][C:54](=[O:55])[CH2:53][O:52][CH2:50][CH3:51])[CH:27]=[N:28]2)=[N:33][CH:32]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 84189Ethoxyacetyl chlorideHCID 589706811-[4-amino-7-bromo-2-(ethoxymethyl)-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl]-2-methylpropan-2-olHCID 67052529Tert-butyl 2-[(3-amino-7-bromo[1,5]naphthyridin-4-yl)amino]-1,1-dimethylethylcarbamate

Product 1

HCID 67052443Tert-butyl 2-({7-bromo-3-[(ethoxyacetyl)amino][1,5]naphthyridin-4-yl}amino)-1,1-dimethylethylcarbamate hydrochlorideYield 66.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

The method described in Part C 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-[(3-amino-7-bromo[1,5]naphthyridin-4-yl)amino]-1,1-dimethylethylcarbamate (64.0 g, 0.156 mol) with ethoxyacetyl chloride (21.0 g, 0.171 mol) in acetonitrile (640 mL). At the completion of the reaction, additional acetonitrile (200 mL) was added, and the solid product was isolated by filtration, washed with a small volume of acetonitrile, and dried for four hours to provide 55.6 g of tert-butyl 2-({7-bromo-3-[(ethoxyacetyl)amino][1,5]naphthyridin-4-yl}amino)-1,1-dimethylethylcarbamate hydrochloride.

Workup

  1. additionwas added
  2. customthe solid product was isolated by filtration
  3. washwashed with a small volume of acetonitrile
  4. customdried for four hours

Sources & evidence

ORD record
ord-b2a2df60325045a2a1d2b185d85a9e5a
Source dataset
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07897609B2

Reaction notes

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