HCID 9911513, compound → HCID 19361844, compound

HRID 376373Notes

Reaction equation

HRID 376373 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:12]([N:18]2[C:26](=[O:27])[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([N+:28]([O-])=O)[CH:24]=3)[C:19]2=[O:31])[CH2:13][S:14]([CH3:17])(=[O:16])=[O:15])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH3:2]>C(OCC)(=O)C.C(Cl)Cl.CCCCCC.[Pd]>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:12]([N:18]2[C:26](=[O:27])[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([NH2:28])[CH:24]=3)[C:19]2=[O:31])[CH2:13][S:14]([CH3:17])(=[O:16])=[O:15])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH3:2]

Participants

6

Reactant 1

HCID 9911513HCID 9911513, compound

Product 1

HCID 19361844HCID 19361844, compoundYield 90%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-[1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-5-nitro-isoindoline-1,3-dione (600 mg, 1.33 mmol) and Pd/C (100 mg, 10%) in ethyl acetate (40 mL) was shaken under hydrogen (50 psi) for 7 h in Parr type shaker. The mixture was filtered through a pad of celite, and the pad was washed with ethyl acetate (50 mL). The filtrate was concentrated in vacuo to give a solid. The solid was stirred in a mixture of methylene chloride (2 mL) and hexane (10 mL). The resulting suspension was filtered to give 2-[1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-5-aminoisoindoline-1,3-dione as a yellow solid (500 mg, 90% yield): mp, 224.5-227.0° C.; 1H NMR (DMSO-d6); δ 1.32 (t, J=6.8 Hz, 3H, CH3), 2.99 (s, 3H, CH3), 3.73 (s, 3H, CH3), 3.73 (s, 3H, CH3), 4.00 (q, J=7 Hz, 2H, CH2), 4.03-4.09 (m, 1H, CHH), 4.34 (dd, J=10.3, 14.2 HZ, 1H, CHH), 5.70 (dd, J=3.7, 10.2 Hz, 1H, NCH), 6.52 (br, s, 2H, NH2), 6.79-6.81 (m, 1H, Ar), 6.92 (br s, 3H, Ar), 7.06 (br s, 1H, Ar), 7.48 (d, J=8.2 Hz, 1H, Ar); 13C NMR (DMSO-d6) δ 14.64, 40.99, 46.99, 53.34, 55.46, 63.80, 106.99, 111.78, 112.31, 116.12, 116.80, 118.61, 125.12, 130.33, 134.11, 147.80, 148.74, 155.13, 167.39, 167.86; Anal Calcd for C20H22NO6S: 57.41; H, 5.30; N, 6.69. Found: C, 57.03; H, 5.40; N, 6.33.

Workup

  1. filtrationThe mixture was filtered through a pad of celite
  2. washthe pad was washed with ethyl acetate (50 mL)
  3. concentrationThe filtrate was concentrated in vacuo
  4. customto give a solid
  5. filtrationThe resulting suspension was filtered

Sources & evidence

ORD record
ord-04a6ea56d100418e8d591c076915edac
Source dataset
uspto-grants-2000_02
Patent number
US06020358

Reaction notes

Loading…