HCID 68769641, compound → HCID 68768163, compound

HRID 1172328Notes

Reaction equation

HRID 1172328 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:21]=[C:22]([CH:27]=[CH:28][CH:29]=2)[C:23]([O:25][CH3:26])=[O:24])=[C:11]([C:30]2[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=2)[CH2:10]1>[Zn].CO.C(O)(=O)C>[NH2:15][C@@H:14]1[CH2:13][C:12]([CH2:18][O:19][C:20]2[CH:21]=[C:22]([CH:27]=[CH:28][CH:29]=2)[C:23]([O:25][CH3:26])=[O:24])=[C:11]([C:30]2[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=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 68769641HCID 68769641, compound

Product 1

HCID 68768163HCID 68768163, compoundYield 76.1%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 10129899Acetic acid methanolSolvent

Procedure

To a solution of Example 9A (35 mg, 0.068 mmol) in mixture of methanol/acetic acid (0.5 mL/0.5 mL) Zn powder (45 mg, 0.68 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 (25 mg, 76%). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.54-8.72 (m, 1H), 7.89-8.11 (m, 2H), 6.96-7.72 (m, 8H), 4.46-4.58 (m, 2H), 3.80-3.87 (m, 4H), 3.59-3.72 (m, 1H), 2.53-2.88 (m, 4H). MS (ESI) m/z 483 (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-660e5504c35c48299ad6e8b5e23ce3e1
Source dataset
uspto-grants-2010_11
Patent number
US07834012B2

Reaction notes

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