Diisopropylethylamine → HCID 178432836, compound

HRID 1893383Notes

Reaction equation

HRID 1893383 reaction equation
Cl.[Cl:2][C:3]1[CH:28]=[CH:27][C:6]2[N:7]3[C:11]([CH2:12][NH:13][CH2:14][C:5]=2[CH:4]=1)=[N:10][N:9]=[C:8]3[C@H:15]1[CH2:20][CH2:19][C@H:18]([C:21]2[N:25]=[C:24]([CH3:26])[O:23][N:22]=2)[CH2:17][CH2:16]1.C(N(C(C)C)C(C)C)C.FC(F)(F)S(O[CH2:44][CH:45]([F:47])[F:46])(=O)=O>ClCCl>[Cl:2][C:3]1[CH:28]=[CH:27][C:6]2[N:7]3[C:11]([CH2:12][N:13]([CH2:44][CH:45]([F:47])[F:46])[CH2:14][C:5]=2[CH:4]=1)=[N:10][N:9]=[C:8]3[C@H:15]1[CH2:20][CH2:19][C@H:18]([C:21]2[N:25]=[C:24]([CH3:26])[O:23][N:22]=2)[CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27740892,2-Difluoroethyl trifluoromethanesulfonateHCID 178432835HCID 178432835, compound

Product 1

HCID 178432836HCID 178432836, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of trans-8-chloro-1-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)-cyclohexyl]-5,6-dihydro-4H-2,3,5,10b-tetraaza-benzo[e]azulene hydrochloride (0.100 g, 0.237 mmol) and N-ethyldiisopropylamine (0.122 ml, 0.712 mmol) in dichloromethane (2.4 ml) was added 2,2-difluoroethyl trifluoromethanesulfonate (0.061 g, 0.29 mmol). After stirring for 16 h the reaction mixture was partitioned between ethyl acetate (50 ml) and 0.5 M aqueous sodium hydroxide solution (50 ml). The layers were separated. The aqueous layer was extracted with one 50 ml-portion of ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate and concentrated in vacuo. Flash-chromatography with n-heptane/2-propanol as eluent gave the title compound (0.031 g, 33%) as colorless solid. MS m/e: 449 ([M+H]+).

Workup

  1. customwas partitioned between ethyl acetate (50 ml) and 0.5 M aqueous sodium hydroxide solution (50 ml)
  2. customThe layers were separated
  3. extractionThe aqueous layer was extracted with one 50 ml-portion of ethyl acetate
  4. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e7af6127ba584db5a667c6e58b7e301f
Source dataset
uspto-grants-2013_08
Patent number
US08513238B2

Reaction notes

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