HCID 136124369, compound → HCID 136124374, compound

HRID 494629Notes

Reaction equation

HRID 494629 reaction equation
[C:1]1(=[CH:7][CH2:8][C:9]2([CH3:38])[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]([OH:19])=[C:11]([C:20]3[NH:25][C:24]4[CH:26]=[CH:27][C:28]([NH:30][S:31]([CH3:34])(=[O:33])=[O:32])=[CH:29][C:23]=4[S:22](=[O:36])(=[O:35])[N:21]=3)[C:10]2=[O:37])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H][H]>[Pd].CO.O1CCCC1>[CH:1]1([CH2:7][CH2:8][C:9]2([CH3:38])[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]([OH:19])=[C:11]([C:20]3[NH:25][C:24]4[CH:26]=[CH:27][C:28]([NH:30][S:31]([CH3:34])(=[O:33])=[O:32])=[CH:29][C:23]=4[S:22](=[O:35])(=[O:36])[N:21]=3)[C:10]2=[O:37])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 2

HCID 136124369HCID 136124369, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 136124374HCID 136124374, compoundYield 100.9%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Example 147 (18 mg, 0.032 mmol), 10% palladium on carbon (5 mg) in methanol (5 mL) and tetrahydrofuran (5 mL) was added a hydrogen balloon. After evacuating the solution two times the mixture was stirred under the hydrogen atmosphere at room temperature for 24 hours. The solution was then filtered through celite and the filtrate concentrated to provide the title compound (18 mg, 100%). MS (ESI+) m/z=558 (M+H)+. 1H NMR (300 MHz, DMSO-d6): δ 0.42 (m, 1H), 0.62 (m, 2H), 0.78 (m, 2H), 1.03 (m, 4H), 1.50 (m, 4H), 1.54 (s, 3H), 2.12 (m, 2H), 3.08 (s, 3H), 7.56 (m, 3H), 7.73 (m, 3H), 8.16 (d, J=8.1 Hz, 1H), 10.26 (s, 1H), 13.74 (s, 1H).

Workup

  1. customAfter evacuating the solution two times the mixture
  2. filtrationThe solution was then filtered through celite
  3. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-85636c706c9848feb456fae85ad3fa33
Source dataset
uspto-grants-2009_05
Patent number
US07538105B2

Reaction notes

Loading…