HCID 59128674, compound → HCID 59128662, compound

HRID 1991134Notes

Reaction equation

HRID 1991134 reaction equation
[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([CH:19]=[C:20]([CH3:22])[CH3:21])[CH:18]=[C:13]3[C:12]([C:23]3[N:24]=[C:25]([CH:28]4[CH2:33][CH2:32][N:31]([CH3:34])[CH2:30][CH2:29]4)[S:26][CH:27]=3)=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>CO.[OH-].[OH-].[Pd+2]>[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([CH2:19][CH:20]([CH3:22])[CH3:21])[CH:18]=[C:13]3[C:12]([C:23]3[N:24]=[C:25]([CH:28]4[CH2:29][CH2:30][N:31]([CH3:34])[CH2:32][CH2:33]4)[S:26][CH:27]=3)=[CH:11]2)(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 59128674HCID 59128674, compound

Product 1

HCID 59128662HCID 59128662, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of 75 (166 mg, 0.34 mmol) in MeOH (10 mL) was added 20% Pd(OH)2 on carbon (50 mg, cat.), and the reaction mixture was stirred vigorously under H2 for 72 h. The mixture was then filtered through Celite, which was then washed with MeOH (100 mL). The filtrate was concentrated to afford 76 as a foam (155 mg, 0.31 mmol, 93%). 1H NMR (400 MHz, CDCl3) δ 0.93 (d, J=6.6 Hz, 2H), 1.85-1.97 (m, 1H), 2.06-2.18 (m, 2H), 2.26-2.47 (m, 4H), 2.48 (s, 3H), 2.60 (d, J=7.3 Hz, 2H), 3.10-3.21 (m, 3H), 7.37 (s, 1H), 7.45-7.61 (m, 3H), 8.08 (d, J=2.0 Hz, 1H), 8.15 (s, 1H), 8.21-8.26 (m, 2H), 8.29 (d, J=2.0 Hz, 1H).

Workup

  1. filtrationThe mixture was then filtered through Celite, which
  2. washwas then washed with MeOH (100 mL)
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-8c154548bf4a45cb9ef24790c1059b3e
Source dataset
uspto-grants-2010_01
Patent number
US07645769B2

Reaction notes

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