Triethylamine → 3-(6-Amino-pyridine-3-carbonyl)-1-(6-bromo-pyridin-2-ylmethyl)-1H-quinolin-4-one

HRID 227096Notes

Reaction equation

HRID 227096 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([CH2:8][N:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12](=[O:19])[C:11]([C:20]([C:22]3[CH:23]=[N:24][C:25](Cl)=[CH:26][CH:27]=3)=[O:21])=[CH:10]2)[CH:5]=[CH:4][CH:3]=1.[N-:29]=[N+]=[N-].[Na+].C(N(CC)CC)C.Cl.C(CCP(CCC(O)=O)CCC(O)=O)(O)=O>CN(C=O)C.O>[NH2:29][C:25]1[N:24]=[CH:23][C:22]([C:20]([C:11]2[C:12](=[O:19])[C:13]3[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:9]([CH2:8][C:6]3[CH:5]=[CH:4][CH:3]=[C:2]([Br:1])[N:7]=3)[CH:10]=2)=[O:21])=[CH:27][CH:26]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 33557Sodium AzideHCID 2734570Tris(2-carboxyethyl)phosphine hydrochlorideHCID 57754507HCID 57754507, compound

Product 1

HCID 577545753-(6-Amino-pyridine-3-carbonyl)-1-(6-bromo-pyridin-2-ylmethyl)-1H-quinolin-4-oneYield 62.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

100 mg (0.22 mmol) of 1-(6-bromo-pyridin-2-ylmethyl)-3-(6-chloro-pyridine-3-carbonyl)-1H-quinolin-4-one and 72 mg (1.1 mmol) of sodium azide were heated at 100° C. in 1 mL of DMF for 1 h. The temperature of the solution was lowered to 70° C. and 1 mL of water was added, followed by 214 uL (155 mg, 1.54 mmol) of triethylamine and 378 mg (1.32 mmol) of tris(2-carboxyethyl)phosphine hydrochloride. After 1 h of reaction time the mixture was purified on reverse-phase HPLC, followed by flash chromatography to give 60 mg of a yellow powder. LC-MSD, m/z for C21H15BrN4O2 [M+H]+=435.0, 437.0; HPLC retention time: 0.6 min.

Workup

  1. customwas lowered to 70° C.
  2. customAfter 1 h of reaction time the mixture
  3. customwas purified on reverse-phase HPLC

Sources & evidence

ORD record
ord-dc87f762a0db4bc2bd90e8387eb501ca
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

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