Morpholine → HCID 24953909, compound

HRID 448022Notes

Reaction equation

[I-].[CH2:2]([N:6]1[C:10]([CH3:11])=[C:9]([CH3:12])[S:8]/[C:7]/1=[CH:13]\[C:14]([N:16]1[CH:21]=[CH:20]C(=[N+](C)C)[CH:18]=[CH:17]1)=[O:15])[CH2:3][CH2:4][CH3:5].N1CC[O:28]CC1>O1CCOCC1>[CH2:2]([N:6]1[C:10]([CH3:11])=[C:9]([CH3:12])[S:8]/[C:7]/1=[CH:13]\[C:14]([N:16]1[CH2:21][CH2:20][O:28][CH2:18][CH2:17]1)=[O:15])[CH2:3][CH2:4][CH3:5]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of product from Example 4 (46 mg, 0.1 mmol) and morpholine (175 mg, 2 mmol) in dioxane (10 mL) was heated to 80° C. for 2 hours then concentrated in vacuo. Column chromatography over silica gel (CH2Cl2-MeOH 4:1) provided the title compound. 1H NMR (300 MHz, DMSO-d6) δ 0.96 (t, J=7 Hz, 3H), 1.32 (sextet, J=7 Hz, 2H), 1.53 (quintet, J=7 Hz, 2H), 2.00 (s, 3H), 2.05 (s, 3H), 3.29 (t, J=6 Hz, 4H), 3.55 9t, J=6 Hz, 4H), 3.72 (t, J=7 Hz, 2H), 5.30 (s, 1H); MS (ESI) m/z 297 (M+H).

Workup

concentrationthen concentrated in vacuo

Sources & evidence

ORD record: ord-5ad9318ad5ef4b81981f2b5c7b7bc0ae
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08481574B2

Reaction notes

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