HCID 118704727, compound → HCID 90412574, compound

HRID 1521965Notes

Reaction equation

HRID 1521965 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:37][CH3:38])=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]3[NH:14][C:15]([CH:17]4[CH2:22][CH2:21][CH2:20][N:19]([CH2:23][CH2:24][CH2:25][NH:26]C(=O)OCC5C=CC=CC=5)[CH2:18]4)=[CH:16][C:9]=23)[CH:7]=1.[H][H]>O1CCCC1.CO.[OH-].[OH-].[Pd+2]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:37][CH3:38])=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]3[NH:14][C:15]([CH:17]4[CH2:22][CH2:21][CH2:20][N:19]([CH2:23][CH2:24][CH2:25][NH2:26])[CH2:18]4)=[CH:16][C:9]=23)[CH:7]=1

Participants

6

Reactant 2

HCID 118704727HCID 118704727, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 90412574HCID 90412574, compound

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Example 127 (100 mg, 0.194 mmol) in tetrahydrofuran (20 mL) and methanol (10 mL) was added 20% palladium hydroxide on carbon (wet, 20 mg, 0.015 mmol). The mixture was heated under 50 psi hydrogen at 45° C. for 3 hours and cooled. The insoluble material was filtered off and the filtrate was concentrated. The residue was purified by reverse phase HPLC, and was eluted with 10-70% acetonitrile in 0.1% trifluoroacetic acid/water to afford the title compound. LCMS: 383.23 (M+H)+. 1H NMR (400 MHz, DMSO-d6) δ 1.58-1.74 (m, 3H) 1.82-1.93 (m, 1H) 1.95-2.07 (m, 2H) 2.18 (d, 1H) 2.81-2.97 (m, 4H) 3.14-3.23 (m, 2H) 3.48 (t, 2H) 3.74 (s, 3H) 6.10 (s, 1H) 7.08 (d, 1H) 7.17-7.23 (m, 2H) 7.25-7.34 (m, 1H) 8.22 (d, 1H) 10.17 (s, 1H) 11.88 (s, 1H).

Workup

  1. temperaturecooled
  2. filtrationThe insoluble material was filtered off
  3. concentrationthe filtrate was concentrated
  4. customThe residue was purified by reverse phase HPLC
  5. washwas eluted with 10-70% acetonitrile in 0.1% trifluoroacetic acid/water

Sources & evidence

ORD record
ord-0bb0e46881d848569dc064eba1d6ed5f
Source dataset
uspto-grants-2015_07
Patent number
US09073922B2

Reaction notes

Loading…