Piperidin-4-ol → HCID 10412182, compound

HRID 2376879Notes

Reaction equation

HRID 2376879 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[CH2:8]([CH:10]([NH:13][C:14]([N:16]1[C:24]2[C:19](=[CH:20][C:21]([O:25][C:26]3[CH:31]=[CH:30][N:29]=[C:28]([NH:32][C:33](=[O:41])OC4C=CC=CC=4)[CH:27]=3)=[CH:22][CH:23]=2)[CH:18]=[CH:17]1)=[O:15])[CH2:11][CH3:12])[CH3:9].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>[CH2:11]([CH:10]([NH:13][C:14]([N:16]1[C:24]2[C:19](=[CH:20][C:21]([O:25][C:26]3[CH:31]=[CH:30][N:29]=[C:28]([NH:32][C:33]([N:5]4[CH2:6][CH2:7][CH:2]([OH:1])[CH2:3][CH2:4]4)=[O:41])[CH:27]=3)=[CH:22][CH:23]=2)[CH:18]=[CH:17]1)=[O:15])[CH2:8][CH3:9])[CH3:12]

Participants

5

Reactant 3

HCID 79341Piperidin-4-olHCID 10052324HCID 10052324, compoundHCID 21949162HCID 21949162, compound

Product 1

HCID 10412182HCID 10412182, compoundYield 29.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N,N-Dimethylformamide (4 ml) and 4-hydroxypiperidine (360 mg, 3.56 mmol) were added to a mixture (456 mg) 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 (1.37 mg, 0.294 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-0d8b3af446f4402392f64c9d2d66fa47
Source dataset
uspto-grants-2008_12
Patent number
US07468380B2

Reaction notes

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