Triethylamine → (4-Oxo-1,2,3-benzotriazin-3-yl) 4-[4-(4-chlorophenyl)-9-oxo-11-sulfanylidene-5-oxa-1,10-diazatricyclo[6.3.0.02,6]undeca-2(6),3,7-trien-10-yl]-3,3-dimethylbutanoate

HRID 1713025Notes

Reaction equation

HRID 1713025 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:11]=[C:12]4[C:18](=[O:19])[N:17]([CH2:20][C:21]([CH3:27])([CH3:26])[CH2:22][C:23]([OH:25])=[O:24])[C:16](=[S:28])[N:13]4[C:14]=3[CH:15]=2)=[CH:4][CH:3]=1.O[N:30]1[C:35](=[O:36])[C:34]2[CH:37]=[CH:38][CH:39]=[CH:40][C:33]=2[NH:32][NH:31]1.CCN(CC)CC>C1COCC1.CN(C)C1C=CN=CC=1.CCOC(C)=O.CCCCCC.C(Cl)(Cl)Cl>[O:36]=[C:35]1[N:30]([O:24][C:23](=[O:25])[CH2:22][C:21]([CH3:26])([CH3:27])[CH2:20][N:17]2[C:16](=[S:28])[N:13]3[C:14]4[CH:15]=[C:8]([C:5]5[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=5)[O:9][C:10]=4[CH:11]=[C:12]3[C:18]2=[O:19])[N:31]=[N:32][C:33]2[CH:40]=[CH:39][CH:38]=[CH:37][C:34]1=2

Participants

9

Reactant 3

HCID 8471TriethylamineHCID 98989233-Hydroxy-dihydrobenzotriazinoneHCID 115678964-[2-(4-chloro-phenyl)-6-oxo-4-thioxo-6H-1-oxa-3b,5-diaza-cyclopenta[a]pentalen-5-yl]-3,3-dimethyl-butyric acid

Product 1

HCID 11563127(4-Oxo-1,2,3-benzotriazin-3-yl) 4-[4-(4-chlorophenyl)-9-oxo-11-sulfanylidene-5-oxa-1,10-diazatricyclo[6.3.0.02,6]undeca-2(6),3,7-trien-10-yl]-3,3-dimethylbutanoateYield 27%

Reagents, catalysts & solvents 5

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent2×HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
25 °C

Procedure

Compound 11 (105 mg, 0.25 mmol) was dissolved in dry THF (5 ml) and 3-hydroxy-dihydrobenzotriazinone (HODhbt; 49 mg, 0.3 mmol, 1.2 molequivalents) was added thereto, followed by addition of Et3N (51 mg, 0.5 mmol, 2 molequivalents) and 4-dimethylaminopyridine (DMAP; 15 mg, 0.125 mmol, 0.5 molequivalents). The reaction mixture was stirred at 25° C. for 16 hours while being monitored by TLC using a 6:4 hexane:EtOAc mixture as an eluent, until the appearance of a less polar spot, attributed to the active ester intermediate, was observed. Chloroform was thereafter added and the resulting mixture was washed with 1 M HCl, dried (Na2SO4) and the solvents were removed under reduced pressure to give a red solid. Chromatography was carried out using a 9:1 hexane:ethyl acetate mixture as eluent to give Compound 12 (38 mg, 20% yield) as a orange solid.

Workup

  1. washthe resulting mixture was washed with 1 M HCl
  2. dry with materialdried (Na2SO4)
  3. customthe solvents were removed under reduced pressure
  4. customto give a red solid

Sources & evidence

ORD record
ord-476af68e32884421a708820c17ef12ad
Source dataset
uspto-grants-2010_09
Patent number
US07795255B2

Reaction notes

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