Hydrochloric Acid → HCID 66718503, compound

HRID 2244528Notes

Reaction equation

HRID 2244528 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C@@H:12]([N:18]2[C:26](=[O:27])[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][C:24]=3[NH:28][C:29](=[O:32])[CH2:30][Cl:31])[C:19]2=[O:33])[CH2:13][S:14]([CH3:17])(=[O:16])=[O:15])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH3:2].[CH3:34][NH:35][CH3:36].O1CCCC1.Cl>C(#N)C.C(O)C.C(OCC)(=O)C.CCOCC>[ClH:31].[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C@@H:12]([N:18]2[C:26](=[O:27])[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][C:24]=3[NH:28][C:29](=[O:32])[CH2:30][N:35]([CH3:36])[CH3:34])[C:19]2=[O:33])[CH2:13][S:14]([CH3:17])(=[O:16])=[O:15])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH3:2]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 674DimethylamineHCID 8028TetrahydrofuranHCID 66718542HCID 66718542, compound

Product 1

HCID 66718503HCID 66718503, compoundYield 63%

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of N-{2-[(1R)-1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl]-1,3-dioxoisoindolin-4-yl}-2-chloroacetamide (0.70 g, 1.41 mmol), and dimethylamine in tetrahydrofuran (2.4 mL, 2N, 4.8 mmol) in acetonitrile (15 mL) was stirred at room temperature overnight. The solvent was removed in vacuo to yield an oil. The oil was stirred in ethanol (5 mL). The suspension was filtered and washed with ethanol to give a white solid. To a solution of the solid in ethyl acetate (5 mL) was added hydrogen chloride in ether (1.5 mL, 1N). The resulting suspension was filtered and the solid was washed with ether to give N-{2-[(1R)-1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl]-1,3-dioxoisoindolin-4-yl}-2-(dimethylamino)acetamide hydrogen chloride as a yellow solid (480 mg, 63% yield); mp, 192-194° C.; 1H NMR (DMSO-d6) δ 1.33 (t, J=6.9 Hz, 3H, CH3), 2.87 (s, 6H, 2CH3), 3.03 (s, 3H, CH3), 3.74 (s, 3H, CH3), 4.02 (q, J=7.0 Hz, 2H, CH2), 4.16 (dd, J=4.2, 14.3 Hz, 1H, CHH), 4.25 (brs, 2H, CH2), 4.34 (dd, J=10.8, 14.4 Hz, 1H, CHH), 5.79 (dd, J=4.2, 10.4 Hz, 1H, NCH), 6.92-6.99 (m, 2H, Ar), 7.08 (s, 1H, Ar), 7.69 (d, J=7.3 Hz, 1H, Ar), 7.88 (t, J=7.7 Hz, 1H, Ar), 8.21-8.27 (m, 1H, Ar), 10.29 (s, 1H, HCl), 10.64 (s, 1H, NH); 13C NMR (DMSO-d6) δ 14.65, 41.04, 43.36, 47.23, 52.86, 55.51, 58.09, 63.86, 111.79, 112.39, 119.22, 119.68, 127.78, 127.99, 129.42, 131.76, 134.25, 134.34, 135.95, 147.87, 148.92, 164.60, 166.79; Anal Calcd for C24H29N3O7S+1 HCl: C, 53.38; H, 5.60; N, 7.78; Cl, 6.56. Found: C, 53.52; H, 5.70; N, 7.61; Cl, 6.44.

Workup

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

Sources & evidence

ORD record
ord-d0c8a74ba9a74e42b45005caa7846ca5
Source dataset
uspto-grants-2010_03
Patent number
US07678825B2

Reaction notes

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