Hydrochloric Acid → HCID 68524880, compound

HRID 1836596Notes

Reaction equation

[CH2:1]([N:8]1[CH2:20][C@H:19]2[C@:10](C(OCC)=O)([C:11](=[O:25])[N:12]3[CH2:24][CH2:23][CH2:22][O:21][C:14]4[CH:15]=[CH:16][CH:17]=[C:18]2[C:13]3=4)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>O1CCOCC1>[CH2:1]([N:8]1[CH2:20][C@H:19]2[C@H:10]([C:11](=[O:25])[N:12]3[CH2:24][CH2:23][CH2:22][O:21][C:14]4[CH:15]=[CH:16][CH:17]=[C:18]2[C:13]3=4)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To absolution of (±)-cis ethyl 11-benzyl-9-oxo-6,7,10,11,12,12a-hexahydro-5H-[1,4]oxazepino[2,3,4-ij]pyrrolo[3,4-c]quinoline-9a(9H)-carboxylate (0.45 g, 1.11 mmol) in 20 mL of 1,4-dioxane was added 20 mL of 3N HCl and the resulting mixture was stirred at 100° C. for 24 h. The dioxane and most of the water was removed in vacuo, and the residue was basified with sat'd aq Na2CO3 and extracted with ethyl acetate. The layers were separated and the organics were washed with brine, dried (MgSO4), filtered through a pad of silica gel and concentrated to afford 0.33 g (89%) of the title compound of EXAMPLE 120 as an off-white powder. 1H NMR (CDCl3) δ: 7.41-7.27 (m, 5H), 6.97-6.81 (m, 3H), 4.60 (dt, 1H), 4.40 (ddd, 1H), 4.13 (ddd, 1H), 3.85-3.75 (m, 1H), 3.82 (broad s, 2H), 3.68-3.57 (m, 1H), 3.52-3.40 (m, 2H), 3.28-3.20 (m, 1H), 3.20-3.10 (m, 1H), 2.56 (t, 1H, J=9.9 Hz), 2.25-2.10 (m, 2H). LRMS (ES)+: 335.4 (M+H)+.

Workup

customThe dioxane and most of the water was removed in vacuo
extractionextracted with ethyl acetate
customThe layers were separated
washthe organics were washed with brine
dry with materialdried (MgSO4)
filtrationfiltered through a pad of silica gel
concentrationconcentrated

Sources & evidence

ORD record: ord-af4c5c8c7d5245f692ada08e4034d817
Source dataset: uspto-grants-2004_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06777406B2

Reaction notes

Loading…