Hydrochloric Acid → HCID 67164302, compound

HRID 902965Notes

Reaction equation

HRID 902965 reaction equation
[CH2:1]([N:3]([CH2:28][CH3:29])[CH2:4][CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]2[C:14]3[CH:15]=[CH:16][C:17]([O:19][CH2:20][CH2:21][N:22]([CH2:25][CH3:26])[CH2:23][CH3:24])=[CH:18][C:13]=3[S:12][C:11]=2[CH:27]=1)[CH3:2].[ClH:30].O1CCOCC1>C(OCC)(=O)C.C(O)C>[ClH:30].[ClH:30].[CH2:28]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]2[C:14]3[CH:15]=[CH:16][C:17]([O:19][CH2:20][CH2:21][N:22]([CH2:25][CH3:26])[CH2:23][CH3:24])=[CH:18][C:13]=3[S:12][C:11]=2[CH:27]=1)[CH3:29]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 11429912HCID 11429912, compound

Product 1

HCID 67164302HCID 67164302, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of the product of Example 16A (250 mg, 0.60 mmol) in ethyl acetate (5 mL) and ethanol (0.2 mL), was added a solution of HCl in dioxane (4M; 0.33 mL, 1.32 mmol; Aldrich). After stirring the mixture for 6 hours, the resulting solid was collected by filtration to afford the title compound (284 mg, 0.50 mmol; 93%). 1H NMR (300 MHz, methanol-d4): δ 8.05 (2H, d, J=9 Hz), 7.54 (2H, d, J=2 Hz), 7.16 (2H, dd, J=9, 2 Hz), 4.46 (4H, t, J=5 Hz), 3.68 (4H, t, J=5 Hz), 3.44-3.35 (8H, q, J=7 Hz), 1.40 (12H, t, J=7 Hz). MS (DCl/NH3): m/z 415 (M+1)+. Anal. Calcd. for C24H34N2O2S.2HCl.0.2C4H8O2: C, 58.97; H, 7.50; N, 5.55. Found: C, 58.94; H, 7.43; N, 5.52.

Workup

  1. filtrationthe resulting solid was collected by filtration

Sources & evidence

ORD record
ord-9ff1cfba4e814c2dbccee8cb408362a8
Source dataset
uspto-grants-2008_04
Patent number
US07365193B2

Reaction notes

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