Morpholine → HCID 10433960, compound

HRID 2376875Notes

Reaction equation

HRID 2376875 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[CH3:7][CH:8]([CH3:40])[CH2:9][CH2:10][NH:11][C:12]([N:14]1[C:22]2[C:17](=[CH:18][C:19]([O:23][C:24]3[CH:29]=[CH:28][N:27]=[C:26]([NH:30][C:31](=O)[O:32]C4C=CC=CC=4)[CH:25]=3)=[CH:20][CH:21]=2)[CH:16]=[CH:15]1)=[O:13].CC(C)CCNC(N1C2C(=CC(OC3C=CN=C(NC(N4CCC(N5CCCC5)CC4)=O)C=3)=CC=2)C=C1)=O>CN(C)C=O>[CH3:7][CH:8]([CH3:40])[CH2:9][CH2:10][NH:11][C:12]([N:14]1[C:22]2[C:17](=[CH:18][C:19]([O:23][C:24]3[CH:29]=[CH:28][N:27]=[C:26]([NH:30][C:31]([N:1]4[CH2:6][CH2:5][O:4][CH2:3][CH2:2]4)=[O:32])[CH:25]=3)=[CH:20][CH:21]=2)[CH:16]=[CH:15]1)=[O:13]

Participants

5

Reactant 3

HCID 8083MorpholineHCID 10324324HCID 10324324, compoundHCID 21949214HCID 21949214, compound

Product 1

HCID 10433960HCID 10433960, compoundYield 34.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N,N-dimethylformamide (5 ml) and morpholine (0.163 ml, 1.87 mmol) were added to a mixture (0.6 g) of phenyl N-(4-(1-((3-methylbutyl)amino)carbonyl-1H-5-indolyl)oxy-2-pyridyl)carbamate and phenyl N-(4-(1-((3-methylbutyl)amino)carbonyl-1H-5-indolyl)oxy-2-pyridyl)-N-(phenoxycarbonyl)carbamate synthesized in Example 93; 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 (0.202 g, 0.447 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-4ea960b0b7c54a27b6aec1794f837b88
Source dataset
uspto-grants-2008_12
Patent number
US07468380B2

Reaction notes

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