Morpholine → HCID 46868294, compound

HRID 506786Notes

Reaction equation

[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C([O-])([O-])=O.[K+].[K+].[Cl:13][C:14]1[CH:19]=[CH:18][N:17]=[C:16]2[N:20]([S:39]([C:42]3[CH:47]=[CH:46][C:45]([CH3:48])=[CH:44][CH:43]=3)(=[O:41])=[O:40])[C:21]([C:23]3[C:27]4=[N:28][C:29]([O:34][CH3:35])=[C:30]([O:32][CH3:33])[CH:31]=[C:26]4[N:25]([CH2:36][CH2:37]I)[CH:24]=3)=[CH:22][C:15]=12>CC#N>[Cl:13][C:14]1[CH:19]=[CH:18][N:17]=[C:16]2[N:20]([S:39]([C:42]3[CH:43]=[CH:44][C:45]([CH3:48])=[CH:46][CH:47]=3)(=[O:40])=[O:41])[C:21]([C:23]3[C:27]4=[N:28][C:29]([O:34][CH3:35])=[C:30]([O:32][CH3:33])[CH:31]=[C:26]4[N:25]([CH2:36][CH2:37][N:1]4[CH2:6][CH2:5][O:4][CH2:3][CH2:2]4)[CH:24]=3)=[CH:22][C:15]=12

Participants

Conditions

Temperature: 60 °C

Procedure

Add morpholine (3.5 equiv., 25.9 mg, 26.1 μmol, 0.30 mmol) and K2CO3 (11.7 mg, 0.085 mmol) to bisazaindole 32 (54 mg, 0.0848 mmol) in CH3CN (6.0 mL). After heating at 60° C. for 30 h, concentrate the reaction medium under vacuum and submit the residue of raw product to flash chromatography on SiO2 (MeOH at 2-4%/CH2Cl2) to obtain 33 (40 mg, 79.2%) as an ivory-colored solid: 1H NMR (CDCl3) δ 8.26 (d, 1H, J=5.4 Hz), 7.72 (d, 2H, J=8.4 Hz), 7.66 (s, 1H), 7.16 (m, 3H), 7.09 (d, 2H, J=8.1 Hz), 4.29 (t, 2H, J=6.6 Hz), 4.05 (s, 3H), 4.01 (s, 3H), 3.73 (m, 4H), 2.86 (t, 2H, J=6.6 Hz), 2.55 (m, 4H), 2.33 (s, 3H), TLC (MeOH at 4%/CH2Cl2, 0.25% of NH3) Rf=0.25, m/z obs.=597.56 (M+1)

Workup

concentrationconcentrate the reaction medium under vacuum

Sources & evidence

ORD record: ord-923175072e104d259d22d5d48fba4b73
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07786114B2

Reaction notes

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