HCID 68773226, compound → HCID 68772774, compound

HRID 1172327Notes

Reaction equation

HRID 1172327 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:29]=[N:30][CH:31]=[CH:32][CH:33]=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:21]=[CH:22][C:23]([C:24]#[N:25])=[CH:26][CH:27]=2)=[C:11]([C:28]2[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=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 68773226HCID 68773226, compound

Product 1

HCID 68772774HCID 68772774, compoundYield 53.5%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 10129899Acetic acid methanolSolvent

Procedure

To a solution of Example 8B (40 mg, 0.083 mmol) in a mixture of methanol/acetic acid (0.5 mL/0.5 mL), Zn powder (54 mg, 0.83 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 chromotography (eluting with 0-70% acetonitrile/water and 0.1% trifluoroacetic acid) to provide the title compound (20 mg, 53%). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.34-7.54 (m, 2H), 6.25-6.98 (m, 9H), 5.82-5.96 (m, 2H), 5.73-5.83 (m, 1H), 3.30-3.47 (m, 1H), 1.28-1.80 (m, 4H). MS (ESI) m/z 450 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-708af4d0217c4dd599d81ad8e2254a37
Source dataset
uspto-grants-2010_11
Patent number
US07834012B2

Reaction notes

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