1,2-Dichloroethane → HCID 54591523, compound

HRID 1260201Notes

Reaction equation

HRID 1260201 reaction equation
C(Cl)CCl.[CH3:5][C:6]1[N:10]([CH2:11][C:12]2[CH:13]=[C:14]([N:18]3[CH2:21][CH:20]([OH:22])[CH2:19]3)[CH:15]=[CH:16][CH:17]=2)[N:9]=[C:8]([C:23]2[O:27][N:26]=[C:25]([C:28]3[CH:33]=[CH:32][C:31]([O:34][C:35]([F:38])([F:37])[F:36])=[CH:30][CH:29]=3)[N:24]=2)[CH:7]=1.[CH3:39][N:40]([CH3:45])[CH2:41][C:42](O)=[O:43]>ClCCl.C(OCC)(=O)C>[CH3:39][N:40]([CH3:45])[CH2:41][C:42]([O:22][CH:20]1[CH2:21][N:18]([C:14]2[CH:15]=[CH:16][CH:17]=[C:12]([CH2:11][N:10]3[C:6]([CH3:5])=[CH:7][C:8]([C:23]4[O:27][N:26]=[C:25]([C:28]5[CH:33]=[CH:32][C:31]([O:34][C:35]([F:38])([F:36])[F:37])=[CH:30][CH:29]=5)[N:24]=4)=[N:9]3)[CH:13]=2)[CH2:19]1)=[O:43]

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 673N,N-DimethylglycineHCID 54591302HCID 54591302, compound

Product 1

HCID 54591523HCID 54591523, compoundYield 50.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

86 mg (0.70 mmol) of 4-N,N-dimethylaminopyridine and 671 mg (3.50 mmol) of EDC were added to a solution of 550 mg (1.17 mmol) of the compound from Example 1 and 361 mg (3.50 mmol) of N,N-dimethylglycine in 11 ml of dichloromethane. After the reaction mixture had been stirred at RT for 8 h, all volatile constituents were removed on a rotary evaporator. The residue obtained was taken up in 200 ml of ethyl acetate and washed once with approx. 100 ml of water. After drying over anhydrous magnesium sulphate, filtration and concentration, the product was isolated by means of MPLC (approx. 30 g of silica gel, eluent: 25:25:1 cyclohexane/ethyl acetate/triethylamine) A first fraction of 328 mg of the title compound was obtained. A further 115 mg of the title compound were obtained from a second, still-contaminated fraction by recrystallization from cyclopentyl methyl ether. A total of 443 mg (68% of theory) of the title compound was thus obtained. Another crystallization from diisopropyl ether/cyclopentyl methyl ether (2:1, 1.5 ml per 100 mg) gave the title compound with a melting point of 117° C.

Workup

  1. customall volatile constituents were removed on a rotary evaporator
  2. customThe residue obtained
  3. washwashed once with approx. 100 ml of water
  4. dry with materialAfter drying over anhydrous magnesium sulphate, filtration and concentration

Sources & evidence

ORD record
ord-55a706e153b442b4979bc9dc79e6420a
Source dataset
uspto-grants-2013_06
Patent number
US08470811B2

Reaction notes

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