HCID 22221501, compound → HCID 9861462, compound

HRID 1061580Notes

Reaction equation

HRID 1061580 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][C:12]([N:15]2[CH2:20][CH2:19][N:18]([CH2:21][C:22]3[NH:26][C:25]4[CH:27]=[CH:28][CH:29]=[CH:30][C:24]=4[N:23]=3)[CH2:17][CH2:16]2)=[N:13][CH:14]=1)C1C=CC=CC=1.[H][H]>C(OCC)(=O)C.[Pd]>[NH:23]1[C:24]2[CH:30]=[CH:29][CH:28]=[CH:27][C:25]=2[N:26]=[C:22]1[CH2:21][N:18]1[CH2:19][CH2:20][N:15]([C:12]2[N:13]=[CH:14][C:9]([OH:8])=[CH:10][CH:11]=2)[CH2:16][CH2:17]1

Participants

5

Reactant 2

HCID 22221501HCID 22221501, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 9861462HCID 9861462, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

The product from Example 29D (800 mg) in ethyl acetate (35 mL) was treated with 10% palladium on carbon (85 mg) under a blanket of hydrogen gas at 23° C. until TLC indicated consumption of starting material. The mixture was filtered and the filter cake washed with with methanol and CH2Cl2. The filtrates were combined and concentrated under reduced pressure. The residue was purified by flash chromatography (eluting with 90:10:0.1 CH2Cl2:methanol:NH4OH) to provide the title compound pure as a white solid (566 mg, 92%). mp 144-145° C.; Rf0.08; (95:5 CH2Cl2:methanol:0.1% NH4OH); MS 310 (M+H)+; 1H NMR (300 MHz, MeOD) δ 7.72 (d, 1H, J=2.7 Hz), 7.53 (m, 2H), 7.21 (m, 2H), 7.12 (dd, 1H, J=9, 3 Hz), 6.75 (d, 1H, J=9 Hz), 3.85 (s, 2H), 3.40 (t, 4H, J=5.1 Hz), 2.69 (t, 4H, J=5.1 Hz); Analysis calculated for C17H19N5O (1.0 equivalent methanol, 0.1 equivalent dichloromethane): C, 62.13; H, 6.68; N, 20.01. Found: C, 62.04; H, 6.57; N, 19.67.

Workup

  1. customconsumption of starting material
  2. filtrationThe mixture was filtered
  3. washthe filter cake washed with with methanol and CH2Cl2
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash chromatography (eluting with 90:10:0.1 CH2Cl2:methanol:NH4OH)

Sources & evidence

ORD record
ord-e51537832c874c9cb1f9b4903097070d
Source dataset
uspto-grants-2005_11
Patent number
US06960589B2

Reaction notes

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