Morpholine → HCID 21949119, compound

HRID 2376880Notes

Reaction equation

HRID 2376880 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[CH2:7]([CH:9]([NH:12][C:13]([N:15]1[C:23]2[C:18](=[CH:19][C:20]([O:24][C:25]3[CH:30]=[CH:29][N:28]=[C:27]([NH:31][C:32](=O)[O:33]C4C=CC=CC=4)[CH:26]=3)=[CH:21][CH:22]=2)[CH:17]=[CH:16]1)=[O:14])[CH2:10][CH3:11])[CH3:8].C(C(NC(N1C2C(=CC(OC3C=CN=C(NC(N4CCC(N5CCCC5)CC4)=O)C=3)=CC=2)C=C1)=O)CC)C>CN(C)C=O>[CH2:7]([CH:9]([NH:12][C:13]([N:15]1[C:23]2[C:18](=[CH:19][C:20]([O:24][C:25]3[CH:30]=[CH:29][N:28]=[C:27]([NH:31][C:32]([N:1]4[CH2:6][CH2:5][O:4][CH2:3][CH2:2]4)=[O:33])[CH:26]=3)=[CH:21][CH:22]=2)[CH:17]=[CH:16]1)=[O:14])[CH2:10][CH3:11])[CH3:8]

Participants

5

Reactant 3

HCID 8083MorpholineHCID 10052324HCID 10052324, compoundHCID 21949162HCID 21949162, compound

Product 1

HCID 21949119HCID 21949119, compoundYield 29.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N,N-dimethylformamide (3 ml) and morpholine (0.22 ml, 2.5 mmol) were added to a mixture (0.324 g) of phenyl N-(4-(1-((1-ethylpropyl)amino)carbonyl-1H-5-indolyl)oxy-2-pyridyl)carbamate and phenyl N-(4-(1-((1-ethylpropyl)amino)carbonyl-1H-5-indolyl)oxy-2-pyridyl)-N-(phenoxycarbonyl)carbamate synthesized in Example 96; and the reaction mixture was stirred for 2 hours. The reaction mixture was partitioned between ethyl acetate and water; the organic layer was concentrated; and the residue was purified by silica gel column chromatography (Fuji Silysia NH, ethyl acetate:methanol=10:1) to yield the title compound as white crystals (95 mg, 0.21 mmol).

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. concentrationthe organic layer was concentrated
  3. customand the residue was purified by silica gel column chromatography (Fuji Silysia NH, ethyl acetate:methanol=10:1)

Sources & evidence

ORD record
ord-b5fcac024e964480ae8081a73ab7b4f1
Source dataset
uspto-grants-2008_12
Patent number
US07468380B2

Reaction notes

Loading…