HCID 136383516, compound → HCID 135885195, compound

HRID 2110613Notes

Reaction equation

HRID 2110613 reaction equation
[CH3:1][C:2]([CH3:46])([CH3:45])[CH2:3][CH2:4][C:5]1([NH:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=2[N+:42]([O-])=O)[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([OH:15])=[C:7]([C:16]2[NH:21][C:20]3[CH:22]=[CH:23][C:24]([NH:26][S:27]([CH3:30])(=[O:29])=[O:28])=[CH:25][C:19]=3[S:18](=[O:32])(=[O:31])[N:17]=2)[C:6]1=[O:33]>C(OCC)(=O)C.[Pd]>[NH2:42][C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][C:36]=1[CH2:35][NH:34][C:5]1([CH2:4][CH2:3][C:2]([CH3:46])([CH3:1])[CH3:45])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([OH:15])=[C:7]([C:16]2[NH:21][C:20]3[CH:22]=[CH:23][C:24]([NH:26][S:27]([CH3:30])(=[O:29])=[O:28])=[CH:25][C:19]=3[S:18](=[O:32])(=[O:31])[N:17]=2)[C:6]1=[O:33]

Participants

4

Reactant 1

HCID 136383516HCID 136383516, compound

Product 1

HCID 135885195HCID 135885195, compoundYield 62.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the product of Example 98 (7 mg, 0.01 mmol) in ethyl acetate (0.5 mL) was added 10% Pd/C (2 mg). The mixture was stirred under H2 atmosphere for 1 h and filtered. The filtrate was concentrated in vacuo. Column chromatography on silica (3% methanol/dichloromethane) afforded the title compound as a yellow solid (4 mg, 57%). 1H NMR (300 MHz, DMSO-d6) δ ppm 0.38-0.55 (m, 1H), 0.66 (s, 9H), 0.99-1.14 (m, 1H), 1.86-2.03 (m, 1H), 2.17-2.37 (m, 1H), 3.02 (s, 3H), 3.45-3.57 (m, 1H), 6.55 (t, J=6.25 Hz, 1H), 6.72 (d, J=7.72 Hz, 1H), 6.92 (d, J=7.35 Hz, 1H), 7.00-7.77 (m, 6H), 7.90-8.01 (m, 1H), 8.20 (d, J=6.62 Hz, 1H), 9.97 (s, 1H), 13.90 (s, 1H); MS m/z 638.3 (M+H)+.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-56cceb6359f147c58046a46af7dade6b
Source dataset
uspto-grants-2009_04
Patent number
US07517876B2

Reaction notes

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