Triethylamine → 3-{1-[(6-chloropyrazin-2-yl)amino]ethyl}-N-(5-methylpyridin-3-yl)benzamide

HRID 572212

Reaction equation

HRID 572212 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH:9]([C:11]2[CH:12]=[C:13]([CH:17]=[CH:18][CH:19]=2)[C:14]([OH:16])=O)[CH3:10])[CH:5]=[N:4][CH:3]=1.[CH3:20][C:21]1[CH:22]=[C:23]([NH2:27])[CH:24]=[N:25][CH:26]=1.Cl.CN(C)CCCN=C=NCC.N1(C2C=CN=CC=2)CCCC1.C(N(CC)CC)C>ClCCl>[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH:9]([C:11]2[CH:12]=[C:13]([CH:17]=[CH:18][CH:19]=2)[C:14]([NH:27][C:23]2[CH:24]=[N:25][CH:26]=[C:21]([CH3:20])[CH:22]=2)=[O:16])[CH3:10])[CH:5]=[N:4][CH:3]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 755674-PyrrolidinopyridineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27628943-Amino-5-methylpyridineHCID 866418593-{1-[(6-Chloropyrazin-2-yl)amino]ethyl}benzoic acid

Product 1

HCID 593316333-{1-[(6-chloropyrazin-2-yl)amino]ethyl}-N-(5-methylpyridin-3-yl)benzamideYield 61.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 3-{1-[(6-chloropyrazin-2-yl)amino]ethyl}benzoic acid (11 mg, 0.04 mmol), 5-methylpyridin-3-amine (5 mg, 0.048 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (11 mg, 0.059 mmol), 4-pyrrolidinopyridine (1.2 mg, 0.008 mmol) and triethylamine (0.013 mL, 0.095 mmol) in dichloromethane (1 mL) was stirred at room temperature for 17 hours. After this time the mixture was diluted with dichloromethane (20 mL), washed successively with saturated aqueous sodium hydrogen carbonate (2×15 mL) and brine (15 mL), dried (Na2SO4) and concentrated under reduced pressure to give a dark yellow oil which was purified by flash chromatography (silica, ethyl acetate/methanol) to give 3-{1-[(6-chloropyrazin-2-yl)amino]ethyl}-N-(5-methylpyridin-3-yl)benzamide (9 mg, 61%) as a pale yellow oil.

Workup

  1. washwashed successively with saturated aqueous sodium hydrogen carbonate (2×15 mL) and brine (15 mL)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated under reduced pressure
  4. customto give a dark yellow oil which
  5. customwas purified by flash chromatography (silica, ethyl acetate/methanol)

Sources & evidence

ORD record
ord-54eb7710c91b4e22b485ec28d903e918
Source dataset
uspto-grants-2015_05
Patent number
US09029386B2

Linked notes

Loading…