1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 2-bromo-N-(1-methyl-1-phenylethyl)nicotinamide

HRID 21337Notes

Reaction equation

HRID 21337 reaction equation
[Br:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.CCN=C=NCCCN(C)C.C1C=C2N=NN(O)C2=CC=1.O.[C:33]([NH2:42])([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)([CH3:35])[CH3:34]>CN(C=O)C>[Br:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH:42][C:33]([CH3:35])([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[CH3:34])=[O:6]

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 68509CumylamineHCID 2332622-Bromopyridine-3-carboxylic acidHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 866283362-bromo-N-(1-methyl-1-phenylethyl)nicotinamideYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a similar manner to Step 1 of Example 137, 2-bromonicotinic acid (2.42 g, 12.0 mmol) was dissolved in DMF (48 mL), and the solution was treated with EDCI (3.45 g, 18.0 mmol), HOBT monohydrate (917 mg, 5.99 mmol) and cumylamine (3.40 mL, 24.0 mmol), followed by purification by flash column chromatography (chloroform/methanol=100/1 to 98/2) to obtain 2-bromo-N-(1-methyl-1-phenylethyl)nicotinamide (2.91 g, yield 76%).

Workup

  1. customfollowed by purification by flash column chromatography (chloroform/methanol=100/1 to 98/2)

Sources & evidence

ORD record
ord-8a38407f29b347a89b472a59068b3c64
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Reaction notes

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