Piperidin-4-ol → HCID 9980412, compound

HRID 2376864Notes

Reaction equation

HRID 2376864 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[CH:8]1([NH:11][C:12]([N:14]2[C:22]3[C:17](=[CH:18][C:19]([O:23][C:24]4[CH:29]=[CH:28][N:27]=[C:26]([N:30](C(OC5C=CC=CC=5)=O)[C:31](=[O:39])OC5C=CC=CC=5)[CH:25]=4)=[CH:20][CH:21]=3)[CH:16]=[CH:15]2)=[O:13])[CH2:10][CH2:9]1.C1(NC(N2C3C(=CC(OC4C=CN=C(NC(N5CCC(N6CCCC6)CC5)=O)C=4)=CC=3)C=C2)=O)CC1>CN(C)C=O>[CH:8]1([NH:11][C:12]([N:14]2[C:22]3[C:17](=[CH:18][C:19]([O:23][C:24]4[CH:29]=[CH:28][N:27]=[C:26]([NH:30][C:31]([N:5]5[CH2:6][CH2:7][CH:2]([OH:1])[CH2:3][CH2:4]5)=[O:39])[CH:25]=4)=[CH:20][CH:21]=3)[CH:16]=[CH:15]2)=[O:13])[CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 79341Piperidin-4-olHCID 10435600HCID 10435600, compoundHCID 21949133HCID 21949133, compound

Product 1

HCID 9980412HCID 9980412, compoundYield 59.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N,N-Dimethylformamide (5 ml) and 4-hydroxypiperidine (433 mg, 4.29 mmol) were added to a mixture (470 mg) of phenyl N-(4-(1-cyclopropylaminocarbonyl-1H-5-indolyl)oxy-2-pyridyl)-N-(phenoxycarbonyl)carbamate and phenyl N-(4-(1-cyclopropylaminocarbonyl-1H-5-indolyl)oxy-2-pyridyl)carbamate obtained in Example 68; the reaction mixture was stirred overnight; the reaction mixture was partitioned between ethyl acetate and water; and the organic layer was concentrated to yield the title compound as white crystals (220 mg, 0.51 mmol, 39%).

Workup

  1. customthe reaction mixture was partitioned between ethyl acetate and water
  2. concentrationand the organic layer was concentrated

Sources & evidence

ORD record
ord-95a36359828c4505bd0763c01bcc9db0
Source dataset
uspto-grants-2008_12
Patent number
US07468380B2

Reaction notes

Loading…