Hydrochloric Acid → HCID 66718525, compound

HRID 433302Notes

Reaction equation

HRID 433302 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[C:9](=[O:11])[N:8]([CH:12]([C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH2:27][CH3:28])[CH:19]=1)[CH2:13][S:14]([CH3:17])(=[O:16])=[O:15])[CH2:7]2.[CH3:29][NH:30][CH3:31].[O:32]1CC[CH2:34][CH2:33]1.[ClH:37]>C(#N)C.C(OCC)(=O)C.CCOCC>[ClH:37].[CH3:29][N:30]([CH3:31])[CH2:34][C:33]([NH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[C:9](=[O:11])[N:8]([CH:12]([C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH2:27][CH3:28])[CH:19]=1)[CH2:13][S:14]([CH3:17])(=[O:15])=[O:16])[CH2:7]2)=[O:32]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 674DimethylamineHCID 8028TetrahydrofuranHCID 18758337HCID 18758337, compound

Product 1

HCID 66718525HCID 66718525, compoundYield 74%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolvent2×HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 7-amino-2-[1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl]isoindolin-1-one (1.0 g, 2 mmol), and dimethylamine in tetrahydrofuran (3.6 mL, 2N, 7.2 mmol) in acetonitrile (25 mL) was stirred at room temperature overnight. The solvent was removed in vacuo to give a solid. The solid was recrystallized from ethanol (10 mL) to give a white solid. To stirred solution of the solid in ethyl acetate (10 mL) was added hydrogen chloride in ether (2.5 mL, 1N). After 5 min, ether (10 mL) was added to give a suspension. The suspension was filtered and the solid washed with ether to give 2-(dimethylamino)-N-{2-[1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl]-3-oxoisoindolin-4-yl}acetamide hydrogen chloride as a yellow solid (780 mg, 74% yield); mp, 145-147° C.; 1H NMR (DMSO-d6) δ1.32 (t, J=7 Hz, 3H, CH3), 2.87 (brs, 6H, 2CH3), 3.03 (s, 3H, CH3), 3.73 (s, 3H, CH3), 3.92-4.05 (m, 3H, CHH, CH2), 4.17 (d, J=17.9 Hz, 1H, CHH), 4.31-4.41 (m, 3H, CH2, CHH), 4.68 (d, J=17.9 Hz, 1H, CHH), 5.88 (dd, J=3.5, 10.7 Hz, 1H, NCH), 6.91-6.98 (m, 2H, Ar), 7.02 (s, 1H, Ar), 7.31 (d, J=7.3 Hz, 1H, Ar), 7.59 (t, J=7.9 Hz, 1H, Ar), 8.15 (d, J=8.0 Hz, 1H, Ar), 10.17 (s, 1H, HCl), 10.53 (s, 1H, NH); 13C NMR (DMSO-d6) δ14.72, 40.99, 43.40, 46.20, 48.81, 53.69, 55.32, 58.11, 63.93, 111.98, 112.16, 118.19, 118.58, 119.16, 119.76, 130.01, 133.01, 135.29, 142.55, 148.07, 148.88, 163.88, 167.45; Anal Calcd for C24H31N3O6S+1.1 HCl+1.5 H2O: C, 51.78; H, 6.35; N, 7.55; Cl, 7.00; H2O, 4.85. Found: C, 51.58; H, 6.13; N, 7.39; Cl, 6.87; H2O, 3.34.

Workup

  1. customThe solvent was removed in vacuo
  2. customto give a solid
  3. customThe solid was recrystallized from ethanol (10 mL)
  4. customto give a white solid
  5. waitAfter 5 min
  6. customto give a suspension
  7. filtrationThe suspension was filtered
  8. washthe solid washed with ether

Sources & evidence

ORD record
ord-259651a8d5fe40508e06d888a27ec8ca
Source dataset
uspto-grants-2003_12
Patent number
US06667316B1

Reaction notes

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