1,2-Dichloroethane → HCID 59644753, compound

HRID 1983213Notes

Reaction equation

HRID 1983213 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[S:9]([NH:12][C:13]1[CH:31]=[C:30]([C:32](=[O:36])[NH:33][CH2:34][CH3:35])[CH:29]=[CH:28][C:14]=1[O:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:23]([OH:25])=O)=[CH:18][C:17]=1[O:26][CH3:27])(=[O:11])=[O:10].C(Cl)CCl.C1C=C[C:44]2N(O)N=[N:47][C:45]=2C=1.C(N)C.C1COCC1>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[S:9]([NH:12][C:13]1[CH:31]=[C:30]([CH:29]=[CH:28][C:14]=1[O:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:23](=[O:25])[NH:47][CH2:45][CH3:44])=[CH:18][C:17]=1[O:26][CH3:27])[C:32]([NH:33][CH2:34][CH3:35])=[O:36])(=[O:11])=[O:10]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 6341EthylamineHCID 8028TetrahydrofuranHCID 757711-HydroxybenzotriazoleHCID 9872340HCID 9872340, compound

Product 1

HCID 59644753HCID 59644753, compoundYield 80.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of acid (12) (63 mg, 0.114 mmol), EDC (44 mg, 0.228 mmol), HOBt (18 mg, 0.114 mmol), 114 μL of 2N ethylamine in THF (0.228 mmol) in 1 mL of methylene chloride was allowed to stir for 24 h at room temperature. Upon completion, the solvent was removed and 10 mL of 2N HCl aqueous solution was added and the resulting mixture was extracted with EtOAc (4×20 mL). The combined extracts were washed with water and brine, dried over anhydrous sodium sulfate and concentrated. The residue was purified by column chromatography on a silica gel column using 50% EtOAc/hexane and EtOAc sequentially as the eluents to give 53.0 mg of the title compound. 1H NMR (CDCl3): δ 7.96 (d, J=8.52 Hz, 1H), 7.87 (d, J=2.08 Hz, 1H), 7.83 (br s, 1H), 7.42 (obscured dd, J=8.52, 2.16 Hz, 1H), 7.40 (s, 1H), 7.29 (dd, J=8.12, 2.20 Hz, 1H), 6.90 (d, J=1.72 Hz, 1H), 6.77 (d, J=8.20 Hz, 1H), 6.76 (s, 1H), 6.72 (d, J=8.08 Hz, 1H), 6.54 (d, J=8.52 Hz, 1H), 6.17 (br s, 1H), 5.62 (br s, 1H), 3.67 (s, 3H), 3.52 (s, 2H), 3.45 (m, 2H), 3.29 (m, 2H), 1.23 (dd, J=7.48, 7.48 Hz, 3H), 1.12 (dd, J=7.52, 7.52 Hz, 3H). LCMS (ESI−) 579 (M−1).

Workup

  1. customUpon completion, the solvent was removed
  2. addition10 mL of 2N HCl aqueous solution was added
  3. extractionthe resulting mixture was extracted with EtOAc (4×20 mL)
  4. washThe combined extracts were washed with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography on a silica gel column

Sources & evidence

ORD record
ord-862f9ae777684a6796a05bf84335f106
Source dataset
uspto-grants-2009_06
Patent number
US07541383B2

Reaction notes

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