Triethylamine → N-(3-{(1S)-1-[(6-bromopyridin-2-yl)amino]ethyl}phenyl)-5-methylnicotinamide

HRID 1255830Notes

Reaction equation

HRID 1255830 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C@@H:8]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([Br:17])[N:12]=2)[CH3:9])[CH:5]=[CH:6][CH:7]=1.[CH3:18][C:19]1[CH:20]=[N:21][CH:22]=[C:23]([CH:27]=1)[C:24](O)=[O:25].Cl.CN(C)CCCN=C=NCC.N1(C2C=CN=CC=2)CCCC1.C(N(CC)CC)C>ClCCl>[Br:17][C:13]1[N:12]=[C:11]([NH:10][C@H:8]([C:4]2[CH:3]=[C:2]([NH:1][C:24](=[O:25])[C:23]3[CH:27]=[C:19]([CH3:18])[CH:20]=[N:21][CH:22]=3)[CH:7]=[CH:6][CH:5]=2)[CH3:9])[CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 755674-PyrrolidinopyridineHCID 2562085-Methylnicotinic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86641857N-[(1S)-1-(3-aminophenyl)ethyl]-6-bromopyridin-2-amine

Product 1

HCID 25218464N-(3-{(1S)-1-[(6-bromopyridin-2-yl)amino]ethyl}phenyl)-5-methylnicotinamideYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of N-[(1S)-1-(3-aminophenyl)ethyl]-6-bromopyridin-2-amine (70 mg, 0.24 mmol), 5-methylnicotinic acid (39 mg, 0.29 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (69 mg, 0.36 mmol), 4-pyrrolidinopyridine (7 mg, 0.05 mmol) and triethylamine (0.08 mL, 0.58 mmol) in dichloromethane (3 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/hexanes) to give N-(3-{(1S)-1-[(6-bromopyridin-2-yl)amino]ethyl}phenyl)-5-methylnicotinamide (62 mg, 63%) as a pale yellow foam.

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/hexanes)

Sources & evidence

ORD record
ord-93d9eb6ce7424af4b0ddda5c3c415dd9
Source dataset
uspto-grants-2013_06
Patent number
US08461161B2

Reaction notes

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