Hydrochloric Acid → HCID 131728528, compound

HRID 2425101Notes

Reaction equation

HRID 2425101 reaction equation
S(=O)(=O)(O)O.[Cl:6][C:7]1[C:12]2[O:13][C:14]3[C:23]([CH3:24])=[CH:22][C:21]([C:25]([OH:27])=[O:26])=[CH:20][C:15]=3[S:16](=[O:19])(=[O:18])[CH2:17][C:11]=2[CH:10]=[C:9]([N:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)[CH:8]=1.Cl.[CH:35](O)([CH3:37])[CH3:36]>>[ClH:6].[CH:35]([O:26][C:25]([C:21]1[CH:22]=[C:23]([CH3:24])[C:14]2[O:13][C:12]3[C:7]([Cl:6])=[CH:8][C:9]([N:28]4[CH2:29][CH2:30][NH:31][CH2:32][CH2:33]4)=[CH:10][C:11]=3[CH2:17][S:16](=[O:18])(=[O:19])[C:15]=2[CH:20]=1)=[O:27])([CH3:37])[CH3:36]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 3776Isopropanol2×HCID 11606047HCID 11606047, compound

Product 1

HCID 131728528HCID 131728528, compound

Conditions

Temperature
90 °C

Procedure

Concentrated sulphuric acid (1 mL) was added dropwise to a stirred solution of compound of Example 18 (0.5 g, 1.18 mmol) in dry isopropanol (50 mL) at 90° C. The reaction mixture was stirred at 90° C. for 2 h. Solvent was removed and the residue was taken in chloroform (100 mL) and this was neutralized using sodium carbonate solution (10%). Chloroform layer was washed with water, brine and dried over sodium sulphate. Solvent was removed and the product obtained was converted to hydrochloride salt by using isopropanol/ethereal-HCl to obtain the title compound. Yield: 0.4 g (67.79%); mp: 262-64° C.; 1H NMR (DMSO-d6, 300 MHz): δ 1.29 (d, 6H, 2CH3), 2.63 (s, 3H, CH3), 3.18 (bs, 4H, 2CH2), 3.44 (bs, 4H, 2CH2), 5.11 (s, 1H, CH), 5.17 (s, 2H, CH2), 7.19 (s, 2H, Ar), 8.07 (s, 1H, Ar), 8.11 (s, 1H, Ar), 9.45 (bs, 2H, NH, HCl); MS: m/e (ES+) 465 (M+1, free base).

Workup

  1. customSolvent was removed
  2. washChloroform layer was washed with water, brine
  3. dry with materialdried over sodium sulphate
  4. customSolvent was removed
  5. customthe product obtained

Sources & evidence

ORD record
ord-67ce8916c30947c88ce9bbfb4d3102ab
Source dataset
uspto-grants-2011_06
Patent number
US07964631B2

Reaction notes

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