HCID 68770052, compound → HCID 68771237, compound

HRID 1172326Notes

Reaction equation

HRID 1172326 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C@H:9]1[C@H:14]([N+:15]([O-])=O)[CH2:13][C:12]([CH2:18][O:19][C:20]2[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[CH:22][CH:21]=2)=[C:11]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:10]1>CO.C(O)(=O)C.[Zn]>[NH2:15][C@@H:14]1[CH2:13][C:12]([CH2:18][O:19][C:20]2[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[CH:22][CH:21]=2)=[C:11]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:10][C@H:9]1[C:3]1[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=1[Cl:1]

Participants

4

Reactant 1

HCID 68770052HCID 68770052, compound

Product 1

HCID 68771237HCID 68771237, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 10129899Acetic acid methanolSolvent

Procedure

To a solution of Example 7E (42 mg, 0.088 mmol) in a mixture of methanol/acetic acid (0.75 mL/0.75 mL), Zn powder (57 mg, 0.88 mmol) was added at room temperature. The reaction mixture was stirred for thirty minutes, filtered, concentrated under reduced pressure and purified by high-pressure liquid chromatography (eluting with 0-70% acetonitrile/water and 0.1% trifluoroacetic acid to provide the title compound (30 mg, 76%)). 1H NMR (400 MHz, CDCl3) δ ppm 7.44-7.53 (m, 2H), 7.24-7.39 (m, 4H), 7.12-7.23 (m, 4H), 6.68-6.82 (m, 2H), 4.40-4.51 (m, 1H), 4.27-4.40 (m, 1H), 2.68-2.88 (m, 2H), 2.45-2.64 (m, 2H). MS (ESI) m/z 449 (M+H)+.

Workup

  1. additionwas added at room temperature
  2. filtrationfiltered
  3. concentrationconcentrated under reduced pressure
  4. custompurified by high-pressure liquid chromatography (
  5. washeluting with 0-70% acetonitrile/water and 0.1% trifluoroacetic acid

Sources & evidence

ORD record
ord-c91c7249db5d4f8ca706c1b42a8a9983
Source dataset
uspto-grants-2010_11
Patent number
US07834012B2

Reaction notes

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