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Dimethylformamide → (5,8-Dihydro-6H-[1,7]naphthyridin-7-yl)-acetic acid tert-butyl ester

HRID 82261
Notes
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Reaction equation

HRID 82261 reaction equation
CN(C=O)C.Cl.[N:7]1[C:16]2[CH2:15][NH:14][CH2:13][CH2:12][C:11]=2[CH:10]=[CH:9][CH:8]=1.[C:17]([O:21][C:22](=[O:25])[CH2:23]Br)([CH3:20])([CH3:19])[CH3:18].C(N(CC)CC)C>CCOC(C)=O>[C:17]([O:21][C:22](=[O:25])[CH2:23][N:14]1[CH2:15][C:16]2[N:7]=[CH:8][CH:9]=[CH:10][C:11]=2[CH2:12][CH2:13]1)([CH3:20])([CH3:19])[CH3:18]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 79177tert-Butyl bromoacetateHCID 717209415,6,7,8-Tetrahydro-1,7-naphthyridine hydrochloride

Product 1

HCID 70817261(5,8-Dihydro-6H-[1,7]naphthyridin-7-yl)-acetic acid tert-butyl esterYield 100%

Reagents, catalysts & solvents 1

HCID 8857
Ethyl Acetate
Solvent

Procedure

A DMF solution (8 mL) of 5,6,7,8-Tetrahydro-[1,7]naphthyridinehydrochloride (Preparation 233, 400 mg, 1.93 mmol), bromo-acetic acid tert-butyl ester (414.1 mg, 2.12 mmol) and triethylamine (1.64 mL, 11.92 mmol) was heated at 80° C. for 16 hours. The reaction mixture was diluted with EtOAc (40 mL), washed with water (3×25 mL), brine (20 mL), dried over Na2SO4 and evaporated to dryness in vacuo to afford the title compound as colorless sticky solid in 100% yield, 480 mg.

Workup

  1. washwashed with water (3×25 mL), brine (20 mL)
  2. dry with materialdried over Na2SO4
  3. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-1725a5b1d7884bd9b6deab6088ac39ef
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08846698B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes