Hydrochloric Acid → HCID 66718509, compound

HRID 433299Notes

Reaction equation

HRID 433299 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]([N:17]2[C:25](=[O:26])[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][C:23]=3[NH:27][C:28](=[O:31])[CH2:29][Cl:30])[C:18]2=[O:32])[CH2:12][S:13]([CH3:16])(=[O:15])=[O:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[CH3:33][NH:34][CH3:35].O1CCCC1.Cl>C(#N)C.C(O)C.C(OCC)(=O)C.CCOCC>[ClH:30].[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]([N:17]2[C:25](=[O:26])[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][C:23]=3[NH:27][C:28](=[O:31])[CH2:29][N:34]([CH3:35])[CH3:33])[C:18]2=[O:32])[CH2:12][S:13]([CH3:16])(=[O:15])=[O:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 674DimethylamineHCID 8028TetrahydrofuranHCID 18758324HCID 18758324, compound

Product 1

HCID 66718509HCID 66718509, compoundYield 74%

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent2×HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of N-{2-[1-(3,4-dimethoxyphenyl)-2-(methylsulfonyl)ethyl]-1,3-dioxoisoindolin-4-yl}-2-chloroacetamide (1.3 g, 2.7 mmol), and dimethylamine in tetrahydrofuran (4.5 mL, 2N, 9.0 mmol) in acetonitrile (20 mL) was stirred at room temperature overnight. The solvent was removed in vacuo to give an oil. The oil was stirred in ethanol (5 mL). The resulting suspension was filtered and the solid washed with ethanol to give a yellow solid. To a stirred solution of the solid in ethyl acetate (10 mL) was added hydrogen chloride in ether (3.0 mL, 1N). After 5 min, ether (10 mL) was added. The resulting suspension was filtered and washed with ether to yield N-{2-[1-(3,4-dimethoxyphenyl)-2-(methylsulfonyl)ethyl]-1,3-dioxoisoindolin-4-yl}-2-(dimethylamino)acetamide hydrogen chloride as a yellow solid (1.07 g, 74% yield); mp, 178-180° C.; 1H NMR (DMSO-d6) δ2.69 (brs, 6H, 2CH3), 3.02 (s, 3H, CH3), 3.73 (s, 3H, CH3), 3.77 (s, 3H, CH3), 3.88 (brs, 2H, CH2), 4.16 (dd, J=4.2, 14.3 Hz, 1H, CHH), 4.34 (dd, J=10.8, 14.4 Hz, 1H, CHH), 5.79 (dd, J=4.2, 10.4 Hz, 1H, NCH), 6.92-6.97 (m, 2H, Ar), 7.10 (d, J=1.4 Hz, 1H, Ar), 7.65 (d, J=7.2 Hz, 1H, Ar), 7.85 (t, J=7.7 Hz, 1H, Ar), 8.37-8.40 (m, 1H, Ar), 10.15 (s, 1H, HCl), 10.68 (s, 1H, NH); 13C NMR (DMSO-d6) δ41.06, 44.18, 47.31, 52.95, 55.55, 55.59, 59.85, 111.26, 111.65, 119.16, 119.69, 127.00, 129.49, 121.64, 134.99, 136.09, 148.71, 148.76, 166.92, 167.34; Anal Calcd for C23H27N3O7S+1.25 HCl+0.4 H2O: C, 50.94; H, 5.40; N, 7.75; Cl, 8.17; H2O, 1.33. Found: C, 51.30; H, 5.50; N, 7.37; Cl, 8.28; H2O, 1.68.

Workup

  1. customThe solvent was removed in vacuo
  2. customto give an oil
  3. filtrationThe resulting suspension was filtered
  4. washthe solid washed with ethanol
  5. customto give a yellow solid
  6. waitAfter 5 min
  7. filtrationThe resulting suspension was filtered
  8. washwashed with ether

Sources & evidence

ORD record
ord-b8f59690288c4c9c853952a2e0927469
Source dataset
uspto-grants-2003_12
Patent number
US06667316B1

Reaction notes

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