Hydrochloric Acid → HCID 69433929, compound

HRID 969987Notes

Reaction equation

HRID 969987 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]([O:9][C:10]1[N:15]=[CH:14][C:13]([C:16]3[CH:17]=[C:18]([CH:20]=[CH:21][CH:22]=3)[NH2:19])=[CH:12][CH:11]=1)[CH2:2]2.[ClH:23].O1CCOCC1>C(OCC)(=O)C>[ClH:23].[N:1]12[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8]1)[CH:3]([O:9][C:10]1[N:15]=[CH:14][C:13]([C:16]3[CH:17]=[C:18]([CH:20]=[CH:21][CH:22]=3)[NH2:19])=[CH:12][CH:11]=1)[CH2:2]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 11437893HCID 11437893, compound

Product 1

HCID 69433929HCID 69433929, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The product of Example 12B (50 mg, 0.17 mmol) in ethyl acetate (5 mL) was treated with 4M HCl in 1,4-dioxane (0.2 mL, 0.8 mmol) at ambient temperature for 10 hours. The title compound was obtained as a solid (30 mg, yield, 44%). 1H NMR (MeOH-d4, 300 MHz) δ 1.90-2.25 (m, 3H), 2.30-2.45 (m, 1H), 2.70-2.76 (m, 1H), 3.37-3.52 (m, 5H), 3.90-3.98 (m, 1H), 5.42-5.50 (m, 1H), 6.71 (s, 2.5H), 6.81-6.89 (m, 1H), 7.03 (d, J=8.9 Hz, 1H), 7.41 (ddd, J=7.8, 2.4, 1.0 Hz, 1H), 7.60-7.68 (m, 2H), 7.75 (dt, J=7.8, 1.0 Hz, 1H), 8.05 (dd, J=8.8, 2.7 Hz, 1H), 8.45 (d, J=2.7 Hz, 1H) ppm. MS (DCl/NH3) m/z 296 (M+H)+. Anal. Calculated for C18H21N3O.3.3HCl.1.0H2O: C, 49.85; H, 6.11; N, 9.69. Found: C, 49.93; H, 5.77; N, 9.51.

Sources & evidence

ORD record
ord-821e4c4c2a664affbe2a3a82dc1068f1
Source dataset
uspto-grants-2007_12
Patent number
US07309699B2

Reaction notes

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