HCID 69202573, compound → HCID 11428656, compound

HRID 270690Notes

Reaction equation

HRID 270690 reaction equation
[NH2:1][C:2]1[CH2:3][C:4](=[O:17])[N:5]([C:7]2[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=2)[N:6]=1.CN(C)[CH:20]=[CH:21][C:22]([C:24]1[C:29]([CH3:30])=[CH:28][CH:27]=[CH:26][N:25]=1)=O>N1C=CC=CC=1>[CH3:30][C:29]1[C:24]([C:22]2[N:1]=[C:2]3[NH:6][N:5]([C:7]4[CH:8]=[CH:9][C:10]([C:13]([F:16])([F:14])[F:15])=[CH:11][CH:12]=4)[C:4](=[O:17])[C:3]3=[CH:20][CH:21]=2)=[N:25][CH:26]=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 69202573HCID 69202573, compoundHCID 69203985HCID 69203985, compound

Product 1

HCID 11428656HCID 11428656, compoundYield 23.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of the product of Step 1 (1.68 g, 0.0074 mol) and 3-(dimethylamino)-1-(3-methyl-2-pyridinyl)-2-propen-1-one (EP-A-0233461) (1.4 g, 0.0074 mol) in pyridine (20 mL) was heated at reflux for 3 h. The mixture was concentrated and then triturated to give a solid which was recrystallised from iPrOH to give 0.64 g (23% yield) of product as a yellow powder. 1H NMR (360 MHz, DMSO): 2.6 (3H, s), 7.45-7.55 (1H, m), 7.55-7.65 (1H, m), 7.85-7.95 (3H, m), 8.20 (2H, d, J 8.5 Hz), 8.39 (1H, d, J 8.0 Hz), 8.61 (1H, d, J 4.6 Hz).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 h
  3. concentrationThe mixture was concentrated
  4. customtriturated
  5. customto give a solid which
  6. customwas recrystallised from iPrOH

Sources & evidence

ORD record
ord-cd782074d6f2486fb63cdfe6e27092d6
Source dataset
uspto-grants-2008_11
Patent number
US07449585B2

Reaction notes

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