Piperidin-4-ol → HCID 10073189, compound

HRID 2376874Notes

Reaction equation

HRID 2376874 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[CH3:8][CH:9]([CH3:41])[CH2:10][CH2:11][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:40])OC4C=CC=CC=4)[CH:26]=3)=[CH:21][CH:22]=2)[CH:17]=[CH:16]1)=[O:14].CC(C)CCNC(N1C2C(=CC(OC3C=CN=C(NC(N4CCC(N5CCCC5)CC4)=O)C=3)=CC=2)C=C1)=O>CN(C)C=O>[CH3:41][CH:9]([CH3:8])[CH2:10][CH2:11][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:5]4[CH2:6][CH2:7][CH:2]([OH:1])[CH2:3][CH2:4]4)=[O:40])[CH:26]=3)=[CH:21][CH:22]=2)[CH:17]=[CH:16]1)=[O:14]

Participants

5

Reactant 3

HCID 79341Piperidin-4-olHCID 10324324HCID 10324324, compoundHCID 21949214HCID 21949214, compound

Product 1

HCID 10073189HCID 10073189, compoundYield 60.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N,N-dimethylformamide (2.5 ml) and 4-hydroxypiperidine (213 mg, 2.11 mmol) were added to a mixture (243 mg) 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 NH-silica gel column chromatography (ethyl acetate:methanol=10:1) to yield the title compound as white crystals (150 mg, 0.322 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 NH-silica gel column chromatography (ethyl acetate:methanol=10:1)

Sources & evidence

ORD record
ord-49aec44ba9bf455dbfce31dce27cbbcd
Source dataset
uspto-grants-2008_12
Patent number
US07468380B2

Reaction notes

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