3-Bromo-4-methoxybenzoyl chloride → N-(6-Methyl-5,6,7,8-tetrahydro[1,6]naphthyridin-3-yl)-3-bromo-4-methoxybenzamide, monohydrochloride

HRID 1066780Notes

Reaction equation

HRID 1066780 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[CH2:6][CH2:7][N:8]([CH3:12])[CH2:9][C:10]=2[CH:11]=1.[Br:13][C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][C:22]=1[O:23][CH3:24])[C:17]([Cl:19])=[O:18]>O1CCCC1>[ClH:19].[CH3:12][N:8]1[CH2:7][CH2:6][C:5]2[N:4]=[CH:3][C:2]([NH:1][C:17](=[O:18])[C:16]3[CH:20]=[CH:21][C:22]([O:23][CH3:24])=[C:14]([Br:13])[CH:15]=3)=[CH:11][C:10]=2[CH2:9]1

Participants

4

Reactant 2

HCID 27696193-Bromo-4-methoxybenzoyl chlorideHCID 117449583-Amino-5,6,7,8-tetrahydro-6-methyl-1,6-naphthyridine

Product 1

HCID 9866392N-(6-Methyl-5,6,7,8-tetrahydro[1,6]naphthyridin-3-yl)-3-bromo-4-methoxybenzamide, monohydrochloride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3-Amino-6-methyl-5,6,7,8-tetrahydro[1,6]naphthyridine (300 mg; 1.84 mmol) was dissolved in dry tetrahydrofuran (10 ml) under argon and treated with a solution of 3-bromo-4-methoxybenzoyl chloride (459 mg; 1.84 mmol) in dry tetrahydrofuran (10 ml). The mixture was stirred at ambient temperatures for 18 h and the product (720 mg; 95%) collected by filtration washed with tetrahydrofuran and dried.

Workup

  1. filtrationthe product (720 mg; 95%) collected by filtration
  2. washwashed with tetrahydrofuran
  3. customdried

Sources & evidence

ORD record
ord-39e8ab364b194115b701feaf65e42afb
Source dataset
uspto-grants-2001_06
Patent number
US06245778B1

Reaction notes

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