Triethylamine → HCID 66653412, compound

HRID 409539Notes

Reaction equation

HRID 409539 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=[C:28]([C:35]3[CH:40]=[CH:39][CH:38]=[C:37]([C:41]([O:43][CH3:44])=[O:42])[CH:36]=3)[N:27]=2)=[O:25])=[CH:20][C:15]=1[C:16]([O:18][CH3:19])=[O:17].[F:45][C:46]1[CH:53]=[CH:52][C:49]([CH2:50][NH2:51])=[CH:48][CH:47]=1.C(N(CC)CC)C>O1CCOCC1>[F:45][C:46]1[CH:53]=[CH:52][C:49]([CH2:50][NH:51][C:5]([NH:13][C:14]2[CH:23]=[CH:22][C:21]([C:24]([C:26]3[N:30]4[CH:31]=[CH:32][CH:33]=[CH:34][C:29]4=[C:28]([C:35]4[CH:40]=[CH:39][CH:38]=[C:37]([C:41]([O:43][CH3:44])=[O:42])[CH:36]=4)[N:27]=3)=[O:25])=[CH:20][C:15]=2[C:16]([O:18][CH3:19])=[O:17])=[O:11])=[CH:48][CH:47]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 673264-FluorobenzylamineHCID 94429TriphosgeneHCID 66653630HCID 66653630, compound

Product 1

HCID 66653412HCID 66653412, compoundYield 94.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2.14 g (7.2 mmol) of triphosgene are added, at ambient temperature under an inert atmosphere, to 2.58 g (6 mmol) of methyl 2-amino-5-({1-[3-(methoxycarbonyl)phenyl]imidazo[1,5-a]pyridin-3-yl}carbonyl)benzoate in 50 ml of dioxane. After refluxing for 7 hours, 2.25 g (18 mmol) of 4-fluorobenzylamine and 1.82 g (18 mmol) of triethylamine are added at ambient temperature. The reaction medium is refluxed for 3 hours and then concentrated under reduced pressure. The residue is triturated from water. After filtration, the solid is rinsed with methanol and then dried under reduced pressure at 40° C. overnight. 3.3 g of a yellow solid are obtained.

Workup

  1. temperatureAfter refluxing for 7 hours
  2. temperatureThe reaction medium is refluxed for 3 hours
  3. concentrationconcentrated under reduced pressure
  4. customThe residue is triturated from water
  5. filtrationAfter filtration
  6. washthe solid is rinsed with methanol
  7. customdried under reduced pressure at 40° C. overnight

Sources & evidence

ORD record
ord-d1c8637ac9d44738a2648cb1947edff8
Source dataset
uspto-grants-2014_06
Patent number
US08759344B2

Reaction notes

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