Propylamine → HCID 66653584, compound

HRID 409532Notes

Reaction equation

HRID 409532 reaction equation
ClC(Cl)(O[C:5](=[O:11])OC(Cl)(Cl)Cl)Cl.[NH2:13][C:14]1[CH:23]=[CH:22][C:21]([C:24]([C:26]2[N:30]3[CH:31]=[CH:32][CH:33]=[CH:34][C:29]3=[CH:28][N:27]=2)=[O:25])=[CH:20][C:15]=1[C:16]([O:18][CH3:19])=[O:17].[CH2:35]([NH2:38])[CH2:36][CH3:37].C(N(CC)CC)C>O1CCOCC1.O>[CH:28]1[N:27]=[C:26]([C:24]([C:21]2[CH:22]=[CH:23][C:14]([NH:13][C:5](=[O:11])[NH:38][CH2:35][CH2:36][CH3:37])=[C:15]([CH:20]=2)[C:16]([O:18][CH3:19])=[O:17])=[O:25])[N:30]2[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=12

Participants

7

Reactant 4

HCID 7852PropylamineHCID 8471TriethylamineHCID 94429TriphosgeneHCID 66653613HCID 66653613, compound

Product 1

HCID 66653584HCID 66653584, compoundYield 89.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

0.35 g (1.2 mmol) of triphosgene is added, at ambient temperature under a nitrogen atmosphere, to a suspension of 0.5 g (1.7 mmol) of methyl 2-amino-5-(imidazo[1,5-a]pyridin-3-ylcarbonyl)benzoate in 20 ml of anhydrous dioxane. After heating for 2 hours at 100° C., 0.28 ml (3.4 mmol) of n-propylamine and then 0.71 ml (5 mmol) of triethylamine are added to the reaction medium at ambient temperature. After stirring for 18 hours at ambient temperature, H2O is added. The aqueous phase is extracted with dichloromethane. The organic phase is dried over sodium sulphate, filtered, and concentrated under reduced pressure. The yellow solid obtained is purified by silica gel column chromatography, elution being carried out with a dichloromethane/methanol (98/2) mixture. 0.410 g of a yellow solid is obtained.

Workup

  1. extractionThe aqueous phase is extracted with dichloromethane
  2. dry with materialThe organic phase is dried over sodium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe yellow solid obtained
  6. customis purified by silica gel column chromatography, elution

Sources & evidence

ORD record
ord-f4c1355a7eba4c9891951cb348a7d71e
Source dataset
uspto-grants-2014_06
Patent number
US08759344B2

Reaction notes

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