Methanol → HCID 56597375, compound

HRID 409544Notes

Reaction equation

HRID 409544 reaction equation
[S:1](Cl)([CH3:4])(=[O:3])=[O:2].[NH2:6][C:7]1[N:8]=[C:9]([C:16]([C:18]2[CH:19]=[C:20]3[C:25](=[CH:26][CH:27]=2)[NH:24][C:23](=[O:28])[N:22]([CH2:29][CH2:30][CH3:31])[C:21]3=[O:32])=[O:17])[N:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=12.CO>N1C=CC=CC=1>[O:28]=[C:23]1[N:22]([CH2:29][CH2:30][CH3:31])[C:21](=[O:32])[C:20]2[C:25](=[CH:26][CH:27]=[C:18]([C:16]([C:9]3[N:10]4[CH:15]=[CH:14][CH:13]=[CH:12][C:11]4=[C:7]([NH:6][S:1]([CH3:4])(=[O:3])=[O:2])[N:8]=3)=[O:17])[CH:19]=2)[NH:24]1

Participants

5

Reactant 3

HCID 887MethanolHCID 31297Methanesulfonyl chlorideHCID 66653954HCID 66653954, compound

Product 1

HCID 56597375HCID 56597375, compoundYield 32.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

0.1 ml (1.2 mmol) of mesyl chloride is added, at 0° C. under an inert atmosphere, to 0.25 g (0.4 mmol) of 6-[(1-aminoimidazo(1,5-a)pyridin-3-yl)carbonyl]-3-propylquinazoline-2,4(1H,3H)-dione in 5 ml of pyridine. After the addition of methanol, the reaction medium is concentrated under reduced pressure. The residue is taken up with dichloromethane. The organic phase is washed with a 1N aqueous solution of hydrochloric acid and then with water, dried over sodium sulphate, filtered, and concentrated under reduced pressure. The residue is recrystallized while hot from methanol, purified on a silica gel frit, elution being carried out with DMF. 0.057 g of an orange solid is obtained.

Workup

  1. concentrationthe reaction medium is concentrated under reduced pressure
  2. washThe organic phase is washed with a 1N aqueous solution of hydrochloric acid
  3. dry with materialwith water, dried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is recrystallized while hot from methanol
  7. custompurified on a silica gel frit, elution

Sources & evidence

ORD record
ord-c789fc7123c84c55a4422c677c1772ca
Source dataset
uspto-grants-2014_06
Patent number
US08759344B2

Reaction notes

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