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Morpholine → HCID 46868294, compound

HRID 506786
Notes
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Reaction equation

HRID 506786 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 68468406HCID 68468406, compound

Product 1

HCID 46868294HCID 46868294, compoundYield 257.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

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

  1. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes