Morpholine → HCID 46868292, compound

HRID 506774Notes

Reaction equation

I[CH2:2][CH2:3][N:4]1[C:12]2[C:7](=[N:8][C:9]([O:15][CH3:16])=[C:10]([O:13][CH3:14])[CH:11]=2)[C:6]([C:17]2[N:25]([S:26]([C:29]3[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][CH:30]=3)(=[O:28])=[O:27])[C:20]3=[N:21][CH:22]=[CH:23][CH:24]=[C:19]3[CH:18]=2)=[CH:5]1.[NH:36]1[CH2:41][CH2:40][O:39][CH2:38][CH2:37]1.C([O-])([O-])=O.[K+].[K+]>CC#N>[CH3:16][O:15][C:9]1[N:8]=[C:7]2[C:6]([C:17]3[N:25]([S:26]([C:29]4[CH:30]=[CH:31][C:32]([CH3:35])=[CH:33][CH:34]=4)(=[O:28])=[O:27])[C:20]4=[N:21][CH:22]=[CH:23][CH:24]=[C:19]4[CH:18]=3)=[CH:5][N:4]([CH2:3][CH2:2][N:36]3[CH2:41][CH2:40][O:39][CH2:38][CH2:37]3)[C:12]2=[CH:11][C:10]=1[O:13][CH3:14]

Participants

Conditions

Temperature: 60 °C

Procedure

Stir bisazaindole iodide 18 (52 mg, 0.0862 mmol), morpholine (1.10 equiv., 8.26 mg, 8.3 μL, 0.0948 mmol) and K2CO3 (13 mg, 0.0942 mmol), with heating at 60° C. in CH3CN (6 mL) under N2, for 24. LC-MS shows that the reaction is only 50% complete. Add extra morpholine (17 μL) and continue stirring at 60° C. After 48 h, the reaction medium is concentrated under vacuum and the residue is submitted to flash chromatography to give 19 (48 mg, 99%) as a white solid: 1H NMR (CDCl3) δ 8.38 (dd, 1H, J=4.5, 1.2 Hz), 7.75 (dd, 1H, J=4.5, 1.2 Hz), 7.68 (d, 2H, J=8.4 Hz), 7.62 (s, 1H), 7.14 (m, 2H), 7.05 (d, 2H, J=8.4 Hz), 7.02 (s, 1H), 4.28 (t, 2H), 4.05 (s, 3H), 4.0 (s, 3H), 3.74 (m, 4H), 2.90 (t, 2H), 2.55 (m, 4H), 2.29 (s, 3H). TLC (MeOH at 4%/CH2Cl2, 0.25% of NH3) Rf=0.65, m/z obs.=562.15 (M+1)

Workup

concentrationthe reaction medium is concentrated under vacuum

Sources & evidence

ORD record: ord-87c1e8575afe4c4ba3a9e7b453193436
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07786114B2

Reaction notes

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