Dimethylamine → HCID 67215446, compound

HRID 1677575Notes

Reaction equation

HRID 1677575 reaction equation
S(Cl)(Cl)=O.[CH3:5][N:6]([CH3:9])[CH:7]=[O:8].[CH3:10][O:11][C:12]1[CH:13]=[C:14]([CH:29]=[CH:30][C:31]=1[N+:32]([O-:34])=[O:33])[C:15]([C:17]1[N:21]2[CH:22]=[CH:23][CH:24]=[C:25](C(O)=O)[C:20]2=[CH:19][N:18]=1)=[O:16].CNC>ClCCl.O1CCCC1>[CH3:10][O:11][C:12]1[CH:13]=[C:14]([CH:29]=[CH:30][C:31]=1[N+:32]([O-:34])=[O:33])[C:15]([C:17]1[N:21]2[CH:22]=[CH:23][CH:24]=[C:25]([C:7]([N:6]([CH3:9])[CH3:5])=[O:8])[C:20]2=[CH:19][N:18]=1)=[O:16]

Participants

7

Reactant 4

HCID 674DimethylamineHCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 11851972HCID 11851972, compound

Product 1

HCID 67215446HCID 67215446, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

0.17 ml (2.36 mmol) of thionyl chloride and then 30 μl of N,N-dimethylformamide are added to 0.318 g (0.88 mmol) of 3-(3-methoxy-4-nitrobenzoyl)imidazo[1,5-a]pyridine-8-carboxylic acid obtained in example 183 in 10 ml of dichloromethane. The mixture is heated at reflux for 2 hours. The reaction medium is concentrated under reduced pressure. The residue obtained is added to 5 ml of a 2N solution of dimethylamine in tetrahydrofuran. After stirring at ambient temperature for 18 h, the reaction medium is concentrated under reduced pressure. The residue is taken up in dichloromethane. The organic phase is washed with a 1N aqueous hydrochloric acid solution and then with a saturated aqueous sodium chloride solution, dried over sodium sulfate and concentrated under reduced pressure. The residue is purified by column chromatography on silica gel, elution being carried out with dichloromethane and then a dichloromethane/methanol (99/1) mixture. 0.19 g of a yellow solid is collected. Melting point: 176° C.; 1H NMR (d6-DMSO): 4.02 (3H, s), 7.39 (1H, t), 7.53 (1H, d), 7.83 (1H, s), 8.0-8.12 (3H, m), 9.75 (1H, d)

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 2 hours
  3. concentrationThe reaction medium is concentrated under reduced pressure
  4. customThe residue obtained
  5. concentrationthe reaction medium is concentrated under reduced pressure
  6. washThe organic phase is washed with a 1N aqueous hydrochloric acid solution
  7. dry with materialwith a saturated aqueous sodium chloride solution, dried over sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue is purified by column chromatography on silica gel, elution
  10. custom0.19 g of a yellow solid is collected

Sources & evidence

ORD record
ord-fcd8cd9950a84f7da59cc2bfd1f00b9d
Source dataset
uspto-grants-2011_08
Patent number
US08008321B2

Reaction notes

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