HCID 59128661, compound → HCID 59128665, compound

HRID 1991142Notes

Reaction equation

HRID 1991142 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[CH:24]=[N:25][N:26]([CH2:28][CH2:29][N:30]4[CH2:35][CH2:34][O:33][CH2:32][CH2:31]4)[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]([CH3:21])[CH3:22])[CH:18]=[C:13]3[C:12]([C:23]3[CH:24]=[N:25][N:26]([CH2:28][CH2:29][N:30]4[CH2:31][CH2:32][O:33][CH2:34][CH2:35]4)[CH:27]=3)=[CH:11]2)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 59128661HCID 59128661, compound

Product 1

HCID 59128665HCID 59128665, compoundYield 83.3%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of 93 (80 mg, 0.18 mmol) in MeOH (4 mL) was added 20% Pd(OH)2 on C (30 mg, cat.), and the reaction mixture was stirred vigorously under H2 for 24 h. The mixture was then filtered through Celite, which was then washed with MeOH:CH2Cl2=1:1 (v/v; 50 mL). The solutions were combined and concentrated to afford 94 as a foam (66 mg, 0.15 mmol, 82%). 1H NMR (400 MHz, CDCl3) δ 0.84 (d, J=6.6 Hz, 2H), 1.40 (t, J=7.1 Hz, 3H), 1.80 (nonet, J=6.7 Hz, 1H), 2.50 (d, J=7.3 Hz, 2H), 2.49-2.60 (m, 4H), 2.84-3.06 (m, 2H), 3.63-3.76 (m, 4H), 4.29-4.46 (m, 2H), 7.42 (t, J=7.6 Hz, 2H), 7.50 (t, J=7.4 Hz, 1H), 7.66 (d, J=2.0 Hz, 1H), 7.68 (s, 1H), 7.71 (s, 1H), 7.76 (s, 1H), 8.03 (d, J=1.8 Hz, 1H), 8.14 (d, J=7.6 Hz, 1H), 8.20 (d, J=1.9 Hz, 1H).

Workup

  1. filtrationThe mixture was then filtered through Celite, which
  2. washwas then washed with MeOH
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-8c8882c1ee4746cba29920f7c9be30d8
Source dataset
uspto-grants-2010_01
Patent number
US07645769B2

Reaction notes

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