HCID 59843150, compound → HCID 59843267, compound

HRID 2196577Notes

Reaction equation

HRID 2196577 reaction equation
[CH3:1][O:2][C:3]1[CH:30]=[CH:29][CH:28]=[CH:27][C:4]=1[C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH2:15][CH2:16][N:17]([CH2:20][CH2:21][NH:22][CH3:23])[CH2:18][CH:19]=2)=[CH:10][C:9]=1[N+:24]([O-])=O)=[O:6]>CO.C(O)(=O)C.[Zn]>[NH2:24][C:9]1[CH:10]=[C:11]([C:14]2[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][NH:22][CH3:23])[CH2:16][CH:15]=2)[CH:12]=[CH:13][C:8]=1[NH:7][C:5](=[O:6])[C:4]1[CH:27]=[CH:28][CH:29]=[CH:30][C:3]=1[O:2][CH3:1]

Participants

5

Reactant 1

HCID 59843150HCID 59843150, compound

Product 1

HCID 59843267HCID 59843267, compoundYield 27%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

To a solution of 203 (143.9 mg, 0.225 mmol) in MeOH (4.5 mL) and Acetic Acid (1.1 mL) at room temperature was added Zinc dust (85 mg, 1.307 mmol). The solution was stirred 1 h and then filtered and concentrated and the crude residue was purified by flash chromatography (10 to 30% MeOH in DCM) and the material was further triturated with hexane to afford 205 (30 mg, 0.060 mmol, 27%) as a yellow solid. LRMS (ESI): calc. 380.2, found 381.2 (MH)+. 1H-NMR (CDCl3+CD3OD) δ(ppm): 8.15 (dd, J=8.0, 2.2 Hz, 1H), 7.46 (ddd, J=8.8, 8.8, 2.3 Hz, 1H), 7.31 (d, J=8.6 Hz, 1H), 7.07 (dd, 7.4, 7.4 Hz, 1H), 7.00 (d, J=8.2 Hz, 1H), 6.82-6.79 (m, 2H), 3.98 (s, 3H), 3.19-3.16 (m, 2H), 3.08-3.04 (m, 2H), 2.79-2.71 (m, 4H), 2.64 (s, 3H), 2.52-2.47 (m, 2H).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. customthe crude residue was purified by flash chromatography (10 to 30% MeOH in DCM)
  4. customthe material was further triturated with hexane

Sources & evidence

ORD record
ord-8b8e923eaf034fa48f1c508acee913d8
Source dataset
uspto-grants-2012_12
Patent number
US08338437B2

Reaction notes

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