Hydrochloric Acid → HCID 69518453, compound

HRID 1294693Notes

Reaction equation

HRID 1294693 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([S:14][CH:15]2[CH:20]3[CH2:21][CH2:22][N:17]([CH2:18][CH2:19]3)[CH2:16]2)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:23]>C(OCC)(=O)C.O1CCOCC1>[ClH:23].[O:1]([C:8]1[CH:9]=[CH:10][C:11]([S:14][CH:15]2[CH:20]3[CH2:21][CH2:22][N:17]([CH2:18][CH2:19]3)[CH2:16]2)=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 11335924HCID 11335924, compound

Product 1

HCID 69518453HCID 69518453, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

The product of Example 36B (220 mg, 0.71 mmol) in ethyl acetate (5 mL) was treated with 4M HCl in 1,4-dioxane (0.5 mL). The title compound was obtained as a solid (180 mg, yield, 73%). 1H NMR (MeOH-d4, 300 MHz) δ 1.84–2.02 (m, 2H), 2.05–2.20 (m, 2H), 2.37–2.52 (m, 1H), 3.14 (ddd, J=17.6, 10.5 2.4 Hz, 1H), 3.24–3.45 (m, 4H), 3.70–3.79 (m, 2H), 6.92 (dt, J=8.9, 3.0 Hz, 2H), 6.97–7.08(m, 2H), 7.13–7.19 (m, 1H), 7.30–7.42 (m, 2H), 7.50 (dt, J=9.0, 3.0 Hz, 2H) ppm. MS (DCl/NH3) m/z 312 (M+H)+. Anal. calculated for C19H21NOS.1.0HCl.0.9H2O: C, 62.67; H, 6.59; N, 3.85Found: C, 62.31; H, 6.31; N, 4.23.

Sources & evidence

ORD record
ord-1f417c818fbf40d39793c40f4b15ee50
Source dataset
uspto-grants-2007_07
Patent number
US07241773B2

Reaction notes

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