Ethoxyacetyl chloride → N-{7-bromo-4-[(2-hydroxy-2-methylpropyl)amino][1,5]naphthyridin-3-yl}-2-ethoxyacetamide hydrochloride

HRID 909360Notes

Reaction equation

HRID 909360 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[NH:12][CH2:13][C:14]([CH3:17])([OH:16])[CH3:15])=[N:9][CH:8]=[C:7]([Br:18])[CH:6]=2.[CH2:19]([O:21][CH2:22][C:23]([Cl:25])=[O:24])[CH3:20]>C(#N)C>[ClH:25].[Br:18][C:7]1[CH:6]=[C:5]2[C:10]([C:11]([NH:12][CH2:13][C:14]([OH:16])([CH3:15])[CH3:17])=[C:2]([NH:1][C:23](=[O:24])[CH2:22][O:21][CH2:19][CH3:20])[CH:3]=[N:4]2)=[N:9][CH:8]=1

Participants

4

Reactant 2

HCID 84189Ethoxyacetyl chlorideHCID 670523831-[(3-Amino-7-bromo[1,5]naphthyridin-4-yl)amino]-2-methylpropan-2-ol

Product 1

HCID 67052474N-{7-bromo-4-[(2-hydroxy-2-methylpropyl)amino][1,5]naphthyridin-3-yl}-2-ethoxyacetamide hydrochlorideYield 81.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-[(3-amino-7-bromo[1,5]naphthyridin-4-yl)amino]-2-methylpropan-2-ol (100.0 g, 321.4 mmol) and acetonitrile (1 L) was stirred for five minutes, and ethoxyacetyl chloride (43.3 g, 353.3 mmol) was added. The reaction was stirred overnight at room temperature. The solid product was isolated by filtration and washed with acetonitrile (200 mL) to provide 113 g of N-{7-bromo-4-[(2-hydroxy-2-methylpropyl)amino][1,5]naphthyridin-3-yl}-2-ethoxyacetamide hydrochloride as a yellow solid.

Workup

  1. stirringThe reaction was stirred overnight at room temperature
  2. customThe solid product was isolated by filtration
  3. washwashed with acetonitrile (200 mL)

Sources & evidence

ORD record
ord-b3f25160018946ac9b2124effa2f8dbe
Source dataset
uspto-grants-2011_09
Patent number
US08017779B2

Reaction notes

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