Diisopropylethylamine → 6-Chloro-4-(3-iodobenzylamino)nicotinamide

HRID 513290

Reaction equation

HRID 513290 reaction equation
Cl[C:2]1[C:7]([C:8]([NH2:10])=[O:9])=[CH:6][N:5]=[C:4]([Cl:11])[CH:3]=1.[I:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH2:16][NH2:17].CCN(C(C)C)C(C)C>C(C#N)(C)=O>[Cl:11][C:4]1[CH:3]=[C:2]([NH:17][CH2:16][C:15]2[CH:18]=[CH:19][CH:20]=[C:13]([I:12])[CH:14]=2)[C:7]([C:8]([NH2:10])=[O:9])=[CH:6][N:5]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 970123-IodobenzylamineHCID 6000444,6-Dichloronicotinamide

Product 1

HCID 866645466-Chloro-4-(3-iodobenzylamino)nicotinamideYield 97.9%

Reagents, catalysts & solvents 1

HCID 694302-OxopropiononitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4,6-dichloronicotinamide (296 mg, 1.55 mmol) in AcCN (3 mL) was added 3-iodobenzylamine (396 mg, 1.70 mmol) and DIPEA (0.383 mL, 2.32 mmol). After stirring at 80° C. for 15 h, the mixture was concentrated and added water, the resulting precipitate was collected by filtration to give 6-chloro-4-(3-iodobenzylamino)nicotinamide (588 mg).

Workup

  1. concentrationthe mixture was concentrated
  2. additionadded water
  3. filtrationthe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-cb633a02535342f488c2c115d7203c4b
Source dataset
uspto-grants-2015_08
Patent number
US09102625B2

Linked notes

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