HCID 136124369, compound → HCID 136124374, compound

HRID 2224949Notes

Reaction equation

HRID 2224949 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-0048d400ff184232a9341f6b0204770a
Source dataset
uspto-grants-2008_05
Patent number
US07378414B2

Reaction notes

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