Morpholine → HCID 86585721, compound

HRID 1884323Notes

Reaction equation

HRID 1884323 reaction equation
[O:1]=[C:2]1[NH:6][CH:5]2[CH:7]([CH2:10][CH2:11][CH2:12][CH2:13][C:14]([NH:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][O:22][C:23](=[O:46])[CH2:24][C:25]([C:28]3[C:33](=[O:34])[C:32]([CH3:35])=[C:31]([CH2:36][CH2:37][C:38]([O:40]CC=C)=[O:39])[C:30](=[O:44])[C:29]=3[CH3:45])([CH3:27])[CH3:26])=[O:15])[S:8][CH2:9][CH:4]2[NH:3]1.N1CCOCC1>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[O:1]=[C:2]1[NH:6][CH:5]2[CH:7]([CH2:10][CH2:11][CH2:12][CH2:13][C:14]([NH:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][O:22][C:23](=[O:46])[CH2:24][C:25]([C:28]3[C:33](=[O:34])[C:32]([CH3:35])=[C:31]([CH2:36][CH2:37][C:38]([OH:40])=[O:39])[C:30](=[O:44])[C:29]=3[CH3:45])([CH3:27])[CH3:26])=[O:15])[S:8][CH2:9][CH:4]2[NH:3]1

Participants

5

Reactant 2

HCID 8083MorpholineHCID 86585722HCID 86585722, compound

Product 1

HCID 86585721HCID 86585721, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the compound L (34 mg, 53 μmol) in 4 mL of THF was added tetrakis(triphenylphosphine)palladium(0) (6 mg, 5.3 μmol) followed by morpholine (46 μL, 0.53 mmol). After evaporation of the solvent, the residue was purified by flash chromatography using a gradient solvent system 10% MeOH/CH2Cl2 to 100% MeOH to give 12 mg (40%) of the compound M as a yellow solid. 1H NMR 400 MHz (CDCl3) δ7.05 (s, 1H), 6.10 (s, 1H), 5.16 (s, 1H), 4.51 (dd, J=8 Hz, 4.5 Hz, 1H), 4.35 (dd, J=8 Hz, 4.5 Hz, 1H), 3.93 (t, J=7 Hz, 2H), 3.72 (t, J=5.4 Hz, 1H), 3.17 (m, 2H), 2.93 (s, 2H), 2.90 (m, 1H), 2.72 (m, 2H), 2.40 (t, J=8 Hz, 2H), 2.19 (t, J=7.5 Hz, 2H), 2.12 (s, 3H), 1.98 (s, 3H), 1.78-1.52 (br, 6H), 1.52-1.38 (br, 4H), 1.42 (s, 6H), 1.30 (m, 2H).

Workup

  1. customAfter evaporation of the solvent
  2. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-67252c4f06d145e7be40f40ef324ab0b
Source dataset
uspto-grants-2004_07
Patent number
US06764768B2

Reaction notes

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