Ethanol → HCID 66741343, compound

HRID 1027891Notes

Reaction equation

HRID 1027891 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([N:17]2[CH2:23][CH2:22][CH:21]3[CH2:24][CH:18]2[CH2:19][N:20]3C(OCC2C=CC=CC=2)=O)[C:5]2[CH2:12][CH2:11][CH2:10][C:9]3[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=3[C:6]=2[N:7]=1.CCO>C(Cl)Cl.[OH-].[OH-].[Pd+2]>[CH:18]12[CH2:24][CH:21]([NH:20][CH2:19]1)[CH2:22][CH2:23][N:17]2[C:4]1[C:5]2[CH2:12][CH2:11][CH2:10][C:9]3[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=3[C:6]=2[N:7]=[C:2]([NH2:1])[N:3]=1

Participants

5

Reactant 2

HCID 702EthanolHCID 69221921HCID 69221921, compound

Product 1

HCID 66741343HCID 66741343, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 6344DichloromethaneSolvent

Procedure

The product from Example 82A was treated with EtOH (1.5 mL) and 20% Pd(OH)2/C (15 mg), then stirred at ambient temperature under an H2 atmosphere for 16 hours, then diluted with 5:1 CH2Cl2:EtOH, filtered, concentrated and purified by chromatography (eluting with 2, 3.5, 5 and 10% (9:1 MeOH:saturated aqueous NH4OH) in CH2Cl2) to provide the title compound. 1H NMR (CDCl3) δ 1.65-1.86 (m, 2H), 2.01 (d, J=11.53 Hz, 2H), 2.20-2.27 (m, 3H), 2.40-2.49 (m, 1H), 2.62-2.69 (m, 2H), 3.20 (dd, J=11.53, 4.75 Hz, 1H), 3.32 (d, J=12.21 Hz, 1H), 3.46-3.58 (m, 2H), 3.76-3.81 (m, 1H), 4.50 (t, J=4.41 Hz, 1H), 4.71 (s, 2H), 7.20-7.24 (m, 1H), 7.31-7.39 (m, 2H), 7.71-7.75 (m, 1H); MS (M+H)+ m/z 322.

Workup

  1. filtrationEtOH, filtered
  2. concentrationconcentrated
  3. custompurified by chromatography (eluting with 2, 3.5, 5 and 10% (9:1 MeOH:saturated aqueous NH4OH) in CH2Cl2)

Sources & evidence

ORD record
ord-b60fd0305d4149948890657f6ff9a6b9
Source dataset
uspto-grants-2014_05
Patent number
US08735411B2

Reaction notes

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