HCID 131728427, compound → HCID 131728426, compound

HRID 1172341Notes

Reaction equation

HRID 1172341 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][N:19]2[CH2:24][CH2:23][CH2:22][C@@H:21]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:20]2)=[CH:11][CH2:10]1>CO.C(O)(=O)C.[Zn]>[NH2:15][C@@H:14]1[CH2:13][C:12]([CH2:18][N:19]2[CH2:24][CH2:23][CH2:22][C@@H:21]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:20]2)=[CH:11][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 131728427HCID 131728427, compound

Product 1

HCID 131728426HCID 131728426, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 10129899Acetic acid methanolSolvent

Procedure

To a solution of Example 18A (100 mg, 0.24 mmol) in a mixture of methanol/acetic acid (1.0 mL/1.0 mL), Zn powder (170 mg, 2.6 mmol) was added at room temperature. The reaction mixture was stirred for 30 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 (78 mg, 78%). 1H NMR (400 MHz, methanol-d4) δ ppm 7.62 (br s, 1H), 7.51 (br s, 1H), 7.39 (br s, 1H), 6.30-6.20 (m, 1H), 4.21 (q, 2H), 3.95-3.85 (m, 1H), 3.8-3.5 (m, 4H), 3.15-2.80 (m, 4H), 2.75-2.40 (m, 3H), 2.35-2.20 (m, 2H), 2.10-1.90 (m, 2H), 1.65-1.50 (m, 1H), 1.30 (t, 3H). MS (DCI) m/z 411 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-0cb8dad6b4aa4ee4b66a8a848be703d0
Source dataset
uspto-grants-2010_11
Patent number
US07834012B2

Reaction notes

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