Bromotrichloromethane → HCID 67348230, compound

HRID 1672823Notes

Reaction equation

HRID 1672823 reaction equation
[CH3:1][S:2][C:3]1[N:4]=[CH:5][C:6]2[C:15](=[O:16])[N:14]([C:17]3[CH:18]=[C:19]([C:23]4[O:24][CH2:25][C@@H:26]([C:28]([O:30][CH3:31])=[O:29])[N:27]=4)[CH:20]=[CH:21][CH:22]=3)[CH2:13][C@H:12]3[N:8]([CH2:9][CH2:10][CH2:11]3)[C:7]=2[N:32]=1.BrC(Cl)(Cl)Cl.N12CCCC=C1CCCCN2>ClCCl>[CH3:1][S:2][C:3]1[N:4]=[CH:5][C:6]2[C:15](=[O:16])[N:14]([C:17]3[CH:18]=[C:19]([C:23]4[O:24][CH:25]=[C:26]([C:28]([O:30][CH3:31])=[O:29])[N:27]=4)[CH:20]=[CH:21][CH:22]=3)[CH2:13][C@H:12]3[N:8]([CH2:9][CH2:10][CH2:11]3)[C:7]=2[N:32]=1

Participants

5

Reactant 3

HCID 6383BromotrichloromethaneHCID 9834010Diazabicyclo[5.4.0]undec-7-eneHCID 67350582HCID 67350582, compound

Product 1

HCID 67348230HCID 67348230, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl (S)-2-{3-[(S)-9-methylthio-6-oxo-2,3,3a,4-tetrahydro-1H,6H-5,8,10,10b-tetraazabenzo[e]azulen-5-yl]phenyl}-4,5-dihydro-1,3-oxazole-4-carboxylate (138 mg, 0.304 mmol) obtained in Step 1 was dissolved in dichloromethane (5 mL), and the mixture was stirred at room temperature for 2 hours after adding bromotrichloromethane (0.181 mL, 0.913 mmol) and diazabicyclo[5,4,0]undec-7-ene (0.137 mL, 0.913 mmol). The mixture was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography to give methyl (S)-2-[3-(9-methylthio-6-oxo-2,3,3a,4-tetrahydro-1H,6H-5,8,10,10b-tetraazabenzo[e]azulen-5-yl)phenyl]-1,3-oxazole-4-carboxylate (119 mg, 87%).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customthe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-591c280f819b4fdca4bd71fa18dc709d
Source dataset
uspto-grants-2011_08
Patent number
US07998954B2

Reaction notes

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