1,2-Dichloroethane → HCID 178521909, compound

HRID 2252236Notes

Reaction equation

HRID 2252236 reaction equation
[I:1][C:2]1[C:3]2[CH2:13][C:12]3[C:7](=[CH:8][CH:9]=[C:10]([C:14]([OH:16])=O)[CH:11]=3)[C:4]=2[NH:5][N:6]=1.[CH:17]1[CH:18]=[CH:19][C:20]2N(O)N=[N:23][C:21]=2[CH:22]=1.C(Cl)CCl.C1(N)CCCCC1.CCN(CC)CC>CN(C=O)C.CCOC(C)=O>[CH:21]1([NH:23][C:14]([C:10]2[CH:11]=[C:12]3[C:7](=[CH:8][CH:9]=2)[C:4]2[NH:5][N:6]=[C:2]([I:1])[C:3]=2[CH2:13]3)=[O:16])[CH2:22][CH2:17][CH2:18][CH2:19][CH2:20]1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 7965CyclohexylamineHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 178524088HCID 178524088, compound

Product 1

HCID 178521909HCID 178521909, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of Example 84A (0.359 g, 1.07 mmol), HOBt (0.218 g, 1.61 mmol), EDC (0.308, 1.61 mmol), cyclohexylamine (0.18 mL, 1.61 mmol), and Et3N (0.22 mL 1.61 mmol) in DMF (8 mL) was stirred at room temperature overnight. The reaction mixture was diluted with EtOAc and washed with NaHCO3 and brine. The organic layer was dried over MgSO4 filtered, concentrated, and triturated with ether to give 0.216 g (50%) of the desired product as yellow solid. MS (DCI/NH3) m/z: 408.0 (M+H)+; 1H NMR (300 MHz, DMSO46) δ ppm 1.09-1.44 (m, 5H) 1.58-1.91 (m, 5H) 3.48-3.67 (m, 2H) 3.77 (m, 1H) 7.61 (m, 1H) 7.86 (d, J=7.46 Hz, 1H) 8.02 (s, 1H) 8.23 (d, J=8.14 Hz, 1H) 13.27 (s, 0.5H) 13.58 (s, 0.5H).

Workup

  1. washwashed with NaHCO3 and brine
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customtriturated with ether

Sources & evidence

ORD record
ord-eef54e66450d451f880b3cc71949bc1a
Source dataset
uspto-grants-2008_01
Patent number
US07320986B2

Reaction notes

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