Hydrochloric Acid → HCID 69520191, compound

HRID 1294688Notes

Reaction equation

HRID 1294688 reaction equation
[CH3:1][C:2]1[CH:23]=[CH:22][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([NH:13][CH:14]3[CH:19]4[CH2:20][CH2:21][N:16]([CH2:17][CH2:18]4)[CH2:15]3)=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[ClH:24]>C(OCC)(=O)C.O1CCOCC1>[ClH:24].[CH3:1][C:2]1[CH:23]=[CH:22][C:5]([O:6][C:7]2[CH:8]=[CH:9][C:10]([NH:13][CH:14]3[CH:19]4[CH2:20][CH2:21][N:16]([CH2:17][CH2:18]4)[CH2:15]3)=[CH:11][CH:12]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 11324300HCID 11324300, compound

Product 1

HCID 69520191HCID 69520191, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

The product of Example 32A (200 mg, 0.65 mmol) in ethyl acetate (5 mL) was treated with 4M HCl in dioxane (0.5 mL). The title compound was obtained as a solid (180 mg, yield, 73%). 1H NMR (MeOH-d4, 300 MHz) δ 1.96–2.17 (m, 3H), 2.31 (s, 3H), 2.34–2.41 (m, 2H), 3.26–3.54 (m, 5H), 3.81 (ddd, J=12.9, 9.5, 2.4 Hz, 1H), 4.06–4.13 (m, 1H), 6.85 (dt, J=9.0, 2.7 Hz, 2H), 6.97 (dt, J=9.1, 2.7 Hz, 2H) 7.09–7.17 (m, 4H), ppm. MS (DCl/NH3) m/z 309 (M+H)+. Anal. calculated for C20H24N2O.2.0HCl.1.0H2O: C, 60.15; H, 7.07; N, 7.01. Found: C, 60.34; H, 7.14; N, 6.98.

Sources & evidence

ORD record
ord-04fc3be00781451f92474ad0b59394f6
Source dataset
uspto-grants-2007_07
Patent number
US07241773B2

Reaction notes

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