HCID 69225040, compound → HCID 66741460, compound

HRID 1027890Notes

Reaction equation

HRID 1027890 reaction equation
C([N:8]1[CH2:14][CH:13]2[CH2:15][CH:10]([CH2:11][N:12]2[C:16]2[C:17]3[CH2:27][CH2:26][CH2:25][C:24]4[CH:28]=[CH:29][CH:30]=[CH:31][C:23]=4[C:18]=3[N:19]=[C:20]([NH2:22])[N:21]=2)[CH2:9]1)C1C=CC=CC=1>CCO.C(Cl)Cl.[OH-].[OH-].[Pd+2]>[CH:10]12[CH2:15][CH:13]([N:12]([C:16]3[C:17]4[CH2:27][CH2:26][CH2:25][C:24]5[CH:28]=[CH:29][CH:30]=[CH:31][C:23]=5[C:18]=4[N:19]=[C:20]([NH2:22])[N:21]=3)[CH2:11]1)[CH2:14][NH:8][CH2:9]2

Participants

5

Reactant 1

HCID 69225040HCID 69225040, compound

Product 1

HCID 66741460HCID 66741460, compound

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent2×HCID 6344DichloromethaneSolvent

Procedure

The product from Example 81A (69 mg) in EtOH (1.5 mL) was treated with 20% Pd(OH)2/C (35 mg), stirred under an atmosphere of H2 for 16 hours at room temperature, then at 60° C. for 3 hours, after which the reaction was cooled, diluted with 5:1 CH2Cl2:EtOH, stirred for 20 minutes, 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 1.83 (d, J=11.19 Hz, 1H), 1.97-2.08 (m, 1H), 2.09-2.20 (m, 2H), 2.24-2.42 (m, 2H), 2.52 (dt, J=14.50, 5.47 Hz, 1H), 2.61-2.75 (m, 3H), 2.84-2.92 (m, 1H), 2.93-3.01 (m, 1H), 3.31-3.38 (m, 1H), 3.63 (d, J=10.17 Hz, 1H), 3.93 (dd, J=9.83, 5.43 Hz, 1H), 4.43 (dd, J=5.26, 3.56 Hz, 1H), 4.65 (s, 2H), 7.18-7.23 (m, 1H), 7.29-7.39 (m, 2H), 7.72-7.79 (m, 1H); MS (M+H)+ m/z 322.

Workup

  1. waitat 60° C. for 3 hours
  2. temperatureafter which the reaction was cooled
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by chromatography (eluting with 2, 3.5, 5 and 10% (9:1 MeOH:saturated aqueous NH4OH) in CH2Cl2)

Sources & evidence

ORD record
ord-e2f48f2280e94dc98746ba714fc83d04
Source dataset
uspto-grants-2014_05
Patent number
US08735411B2

Reaction notes

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