Dimethylformamide → HCID 21472338, compound

HRID 266054Notes

Reaction equation

HRID 266054 reaction equation
CC1C=C(C)C=C(C)C=1S([O-])(=O)=O.[NH2:14][N+:15]1[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:16]=1.CN(C)C=O.C(=O)([O-])[O-].[K+].[K+].[Br:37][C:38]1[CH:43]=[CH:42][C:41]([C:44](=[O:51])[C:45]#[C:46][CH2:47][CH2:48][CH2:49][CH3:50])=[CH:40][CH:39]=1>O>[CH2:24]([O:23][C:21]([C:17]1[CH:18]=[CH:19][C:20]2[N:15]([N:14]=[C:46]([CH2:47][CH2:48][CH2:49][CH3:50])[C:45]=2[C:44](=[O:51])[C:41]2[CH:42]=[CH:43][C:38]([Br:37])=[CH:39][CH:40]=2)[CH:16]=1)=[O:22])[CH3:25]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium Carbonate3×HCID 12208484HCID 12208484, compound4×HCID 544491361-(4-Bromophenyl) 2-heptyn-1-one

Product 1

HCID 21472338HCID 21472338, compoundYield 45.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 13.8 g of ethyl 1-aminopyridinium 3-carboxylate 2,4,6-trimethylbenzenesulphonate (compound A) (Synthesis 1977, page 1, TAMURA, et al.), 150 ml of dimethylformamide, 5.7 g of potassium carbonate and 10 g of the product of Step A of Example 1 were stirred for 3 hours at room temperature and then 6.9 g of compound A and 2.85 g of potassium carbonate were added. The mixture was stirred for 2 hours. Then 6.9 g of compound A and 2.85 g of potassium carbonate were added and the mixture was stirred for 2 hours at ambient temperature. The mixture was taken up in water and extracted with ethyl acetate. Separation was carried out by chromatography on silica (essence G: 80/ethyl acetate: 20) to obtain 7.38 g of the expected product (M.p.≤50° C.) and 8.25 g of the corresponding isomer of Example 16.

Workup

  1. stirringThe mixture was stirred for 2 hours
  2. stirringthe mixture was stirred for 2 hours at ambient temperature
  3. extractionextracted with ethyl acetate
  4. customSeparation

Sources & evidence

ORD record
ord-ce923dd23ee64f87b8f674d49b86bcc9
Source dataset
uspto-grants-1997_07
Patent number
US05650414

Reaction notes

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