Triethylamine → HCID 21201721, compound

HRID 1979453Notes

Reaction equation

HRID 1979453 reaction equation
N[C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].ClC(Cl)(O[C:17](=[O:23])OC(Cl)(Cl)Cl)Cl.C([N:27](CC)CC)C.[N:32]1([C:37]([CH2:39][N:40]2[C:46]3[CH:47]=[CH:48][CH:49]=[CH:50][C:45]=3[N:44]([CH:51]3[CH2:56][CH2:55][CH2:54][CH2:53][CH2:52]3)[CH2:43][CH:42]([NH2:57])[C:41]2=[O:58])=[O:38])[CH2:36][CH2:35][CH2:34][CH2:33]1>O1CCCC1.C(Cl)(Cl)Cl.O>[N:32]1([C:37]([CH2:39][N:40]2[C:46]3[CH:47]=[CH:48][CH:49]=[CH:50][C:45]=3[N:44]([CH:51]3[CH2:56][CH2:55][CH2:54][CH2:53][CH2:52]3)[CH2:43][CH:42]([NH:57][C:17]([NH:27][C:12]3[CH:11]=[CH:10][C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])=[CH:3][CH:2]=3)=[O:23])[C:41]2=[O:58])=[O:38])[CH2:36][CH2:35][CH2:34][CH2:33]1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 11400Ethyl 3-aminobenzoateHCID 94429TriphosgeneHCID 21202021HCID 21202021, compound

Product 1

HCID 21201721HCID 21201721, compoundYield 226.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
6.5 °C

Procedure

Ethyl 3-aminobenzoate (0.43 g) was dissolved in tetrahydrofuran (25 ml), the solution was cooled to internal temperature 5-8° C. Triphosgene (0.28 g) was added to the solution, and stirred for 5 minutes. Subsequently, triethylamine (0.95 g) was added dropwise over 15 minutes interval. The mixture was stirred at room temperature for 10 minutes, a solution of 1-(pyrrolidin-1-ylcarbonylmethyl)-2-oxo-3-amino-5-cyclohexyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine (0.87 g) in tetrahydrofuran (15 ml) was added to the mixture, the resultant mixture was stirred for one hour. Water and chloroform were added to the reaction mixture and extracted. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, ether was added to crystals so precipitated for trituration, collected by filtration, to thereby obtain 1.20 g of the title compound (Yield: 91.3%).

Workup

  1. stirringThe mixture was stirred at room temperature for 10 minutes
  2. extractionextracted
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure, ether
  6. additionwas added to crystals
  7. customso precipitated for trituration
  8. filtrationcollected by filtration

Sources & evidence

ORD record
ord-f6654d9b9afa4bcf979bc7948213e85f
Source dataset
uspto-grants-2001_05
Patent number
US06239131B1

Reaction notes

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