Morpholine → HCID 145847173, compound

HRID 1264205Notes

Reaction equation

HRID 1264205 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([CH2:17][CH2:18][NH:19]C(OCC=C)=O)=[CH:14][CH:15]=2)[C:10]([C:26](=[NH:35])[NH:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].N1CCOCC1>C(Cl)Cl.[Pd].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>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([CH2:17][CH2:18][NH2:19])=[CH:14][CH:15]=2)[C:10]([C:26](=[NH:35])[NH:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 2

HCID 8083MorpholineHCID 145847176HCID 145847176, compound

Product 1

HCID 145847173HCID 145847173, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 1-tert-Butoxycarbonyl-3-(tert-butoxycarbonylcarbamimidoyl)-5-(2-[allyloxycarbonylamino]ethyl)indole (reference example 8) (0.199 g, 0.409 mmol), 50 mg tetrakis(triphenylphosphine)palladium (0), and 0.078 mL (0.90 mmol) morpholine in 20 mL CH2Cl2 is stirred for one hour. TLC showed some starting material present, so another 50 mg palladium catalyst is added. After stirring 45 minutes, the reaction mixture is concentrated, and the residue chromatographed (10:1 CH2Cl2:7N NH3 in MeOH) to provide the product as a yelow solid. 1H NMR (CDCl3): δ 1.57 (9H, s), 1.64 (9H, s), 2.88 (4H, m), 7.23 (1H, dd, J1=8.7 Hz, J2=1.2 Hz), 7.77 (1H, s), 8.16 (1H, d, J=8.7 Hz), 8.25 (1H, s). MS (EI) m/z 402 M+.

Workup

  1. concentrationthe reaction mixture is concentrated
  2. customthe residue chromatographed (10:1 CH2Cl2:7N NH3 in MeOH)
  3. customto provide the product as a yelow solid

Sources & evidence

ORD record
ord-d12f6ca2664f4d40be3b8877f2950e39
Source dataset
uspto-grants-2003_04
Patent number
US06541505B1

Reaction notes

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