Hydrochloric Acid → HCID 69519557, compound

HRID 1294698Notes

Reaction equation

HRID 1294698 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[CH:8][C:7]([O:17][C:18]1[CH:32]=[CH:31][C:21]([O:22][CH:23]3[CH:28]4[CH2:29][CH2:30][N:25]([CH2:26][CH2:27]4)[CH2:24]3)=[CH:20][CH:19]=1)=[CH:6][CH:5]=2.[ClH:33]>CCOC(C)=O>[ClH:33].[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)=[CH:8][C:7]([O:17][C:18]1[CH:32]=[CH:31][C:21]([O:22][CH:23]3[CH:28]4[CH2:29][CH2:30][N:25]([CH2:26][CH2:27]4)[CH2:24]3)=[CH:20][CH:19]=1)=[CH:6][CH:5]=2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 11258796HCID 11258796, compound

Product 1

HCID 69519557HCID 69519557, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The product of Example 40A (60 mg, 0.14 mmol) was treated with HCl (Aldrich, 4 M in dioxane, 0.25 mL, 1.0 mmol) in EtOAc (5 mL) at ambient temperature for 1 hour to give the title compound as solid (25.0 mg, yield, 39%). 1H NMR (MeOH-d4, 300 MHz) δ 1.78–2.04 (m, 2H), 2.03–2.21 (m, 1H), 2.28–2.37 (m, 1H), 2.37 (s, 3H), 2.45–2.56 (m, 1H), 3.33–3.47 (m, 5H), 3.68–3.86 (m, 1H), 4.73–4.83 (m, 1H), 6.81 (dd, J=8.8, 2.4 Hz, 1H), 6.88–6.98 (m, 4H), 7.09 J=2.4 Hz, 1 H,) 7.25–7.38 (m, 2H), 7.42–7.52 (m, 2H), 7.59–7.69 (m, 2H)ppm. MS (DCl/NH3) m/z 425(M+H)+. Anal. Calculated for C18H28N2O2.1.40HCl.0.62H2O: C, 69.09; H, 6.34; N, 5.76. Found: C, 69.43; H, 5.97; N, 5.43.

Sources & evidence

ORD record
ord-b216e25ad9f7447ab5679a83ab7400e5
Source dataset
uspto-grants-2007_07
Patent number
US07241773B2

Reaction notes

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