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

HRID 1798872
Notes
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Reaction equation

HRID 1798872 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][C:5]([Cl:7])=[O:6].[NH2:8][C:9]1[CH:10]=[N:11][C:12]2[C:17]([C:18]=1[NH:19][CH2:20][C:21]([CH3:24])([OH:23])[CH3:22])=[N:16][CH:15]=[C:14]([Br:25])[CH:13]=2.C(Cl)(Cl)Cl>C(#N)C>[ClH:7].[Br:25][C:14]1[CH:13]=[C:12]2[C:17]([C:18]([NH:19][CH2:20][C:21]([OH:23])([CH3:22])[CH3:24])=[C:9]([NH:8][C:5](=[O:6])[CH2:4][CH2:3][O:2][CH3:1])[CH:10]=[N:11]2)=[N:16][CH:15]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6212ChloroformHCID 27597283-Methoxypropanoyl chlorideHCID 670523831-[(3-Amino-7-bromo[1,5]naphthyridin-4-yl)amino]-2-methylpropan-2-ol

Product 1

HCID 67052276N-{7-bromo-4-[(2-hydroxy-2-methylpropyl)amino][1,5]naphthyridin-3-yl}-3-methoxypropionamide hydrochlorideYield 82%

Reagents, catalysts & solvents 1

HCID 6342
Acetonitrile
Solvent

Procedure

3-Methoxypropionyl chloride (24.90 g, 203 mmol) was added over a period of 5 minutes to a mixture of 1-[(3-amino-7-bromo[1,5]naphthyridin-4-yl)amino]-2-methylpropan-2-ol (52.70 g, 169 mmol), chloroform (100 mL), and acetonitrile (530 mL). The reaction mixture was stirred at ambient temperature overnight. The precipitated solid was isolated by filtration, washed well with acetonitrile, and then dried to provide 60.10 g of N-{7-bromo-4-[(2-hydroxy-2-methylpropyl)amino][1,5]naphthyridin-3-yl}-3-methoxypropionamide hydrochloride as a brown solid, mp 206-208° C.

Workup

  1. customThe precipitated solid was isolated by filtration
  2. washwashed well with acetonitrile
  3. customdried

Sources & evidence

ORD record
ord-69b87c78c377423eb3a62ab4f78ab48b
Source dataset
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08343993B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes