Aniline → HCID 18772036, compound

HRID 888241Notes

Reaction equation

HRID 888241 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[S:8][C:9]([C:13]([OH:15])=O)=[C:10](C)[N:11]=2)[CH:2]=1.[NH2:16]C1C=CC=CC=1>S(Cl)(Cl)=O>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[S:8][C:9]([C:13]([NH2:16])=[O:15])=[CH:10][N:11]=2)[CH:2]=1

Participants

4

Reactant 2

HCID 6115AnilineHCID 27634894-Methyl-2-(pyridin-3-yl)-1,3-thiazole-5-carboxylic acid

Product 1

HCID 18772036HCID 18772036, compound

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Conditions

Temperature
82 °C

Procedure

2-(3-Pyridyl)-4-methylthiazole-5-carboxylic acid (0.61 g, 2.8 mmol) was dissolved in thionyl chloride (2 mL) and the mixture was stirred with heating (82° C., 3 hours). Upon cooling, the solvent was removed and the residue was dried under high vac. The acid chloride was then suspended in 5 mL of pyridine and added to a microwave vial charged with 2-(3-morpholinomethyl)imidazo[2,1-b]thiazol-6-yl)aniline (0.87 g, 2.8 mmol). The reaction was subjected to microwave irradiation (160° C., 15 min). The solution was triturated with methanol, and the resulting solid was filtered and washed with additional methanol. The solid was dried to afford 0.97 g (68%) of 4-methyl-N-(2-(3-morpholinomethyl)imidazo[2,1-b]thiazol-6-yl)phenyl)-2-(pyridin-3-yl)thiazole-5-carboxamide.

Workup

  1. temperatureUpon cooling
  2. customthe solvent was removed
  3. customthe residue was dried under high vac
  4. additionadded to a microwave
  5. customThe reaction was subjected to microwave irradiation (160° C., 15 min)
  6. customThe solution was triturated with methanol
  7. filtrationthe resulting solid was filtered
  8. washwashed with additional methanol
  9. customThe solid was dried

Sources & evidence

ORD record
ord-00243ba6b9754519965d84b2528908eb
Source dataset
uspto-grants-2012_08
Patent number
US08247565B2

Reaction notes

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