Triethylamine → HCID 66653393, compound

HRID 409546Notes

Reaction equation

HRID 409546 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]([Br:35])[N:27]=2)=[O:25])=[CH:20][C:15]=1[C:16]([O:18][CH3:19])=[O:17].[F:36][C:37]1[CH:44]=[CH:43][C:40]([CH2:41][NH2:42])=[CH:39][CH:38]=1.C(N(CC)CC)C>O1CCOCC1.CO.O>[Br:35][C:28]1[N:27]=[C:26]([C:24]([C:21]2[CH:22]=[CH:23][C:14]([NH:13][C:5](=[O:11])[NH:42][CH2:41][C:40]3[CH:43]=[CH:44][C:37]([F:36])=[CH:38][CH:39]=3)=[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

8

Reactant 4

HCID 8471TriethylamineHCID 673264-FluorobenzylamineHCID 94429TriphosgeneHCID 57500383HCID 57500383, compound

Product 1

HCID 66653393HCID 66653393, compoundYield 219.6%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Procedure

3 g (10.4 mmol) of triphosgene diluted in 40 ml of dioxane are added to 5.57 g (14.9 mmol) of methyl 2-amino-5-[1-bromo(imidazo[1,5-a]pyridin-3-yl)carbonyl]benzoate in 160 ml of dioxane, under an inert atmosphere. The reaction medium is refluxed for 1 hour. 3.7 g (0.030 mol) of 4-fluorobenzylamine and 6.22 ml (0.045 mol) of triethylamine are added at ambient temperature. The reaction medium is stirred for 4 hours at ambient temperature and then hydrolysed with water. The precipitate obtained is filtered off, rinsed with water, and dried under reduced pressure at 50° C. overnight. The solid obtained is taken up with methanol, filtered, rinsed with methanol, and dried under reduced pressure overnight. 12 g of a yellow solid are obtained (yield=95.5%).

Workup

  1. temperatureThe reaction medium is refluxed for 1 hour
  2. customThe precipitate obtained
  3. filtrationis filtered off
  4. washrinsed with water
  5. customdried under reduced pressure at 50° C. overnight
  6. customThe solid obtained
  7. filtrationfiltered
  8. washrinsed with methanol
  9. customdried under reduced pressure overnight

Sources & evidence

ORD record
ord-af7c8520f6454eb09ef8e8ff15dca157
Source dataset
uspto-grants-2014_06
Patent number
US08759344B2

Reaction notes

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