Piperidine → N1-Ethyl-5-(2-(piperidin-1-ylcarbonyl)amino-4-pyridyl)oxy-1H-1-indolecarboxamide

HRID 2376861Notes

Reaction equation

HRID 2376861 reaction equation
N1CCCCC1.C(NC(N1C2C(=CC(OC3C=CN=C(NC(=O)OC4C=CC=CC=4)C=3)=CC=2)C=C1)=O)C.[CH2:38]([NH:40][C:41]([N:43]1[C:51]2[C:46](=[CH:47][C:48]([O:52][C:53]3[CH:58]=[CH:57][N:56]=[C:55]([NH:59][C:60]([N:62]4[CH2:67][CH2:66][CH:65](N5CCCC5)[CH2:64][CH2:63]4)=[O:61])[CH:54]=3)=[CH:49][CH:50]=2)[CH:45]=[CH:44]1)=[O:42])[CH3:39]>CN(C)C=O>[CH2:38]([NH:40][C:41]([N:43]1[C:51]2[C:46](=[CH:47][C:48]([O:52][C:53]3[CH:58]=[CH:57][N:56]=[C:55]([NH:59][C:60]([N:62]4[CH2:67][CH2:66][CH2:65][CH2:64][CH2:63]4)=[O:61])[CH:54]=3)=[CH:49][CH:50]=2)[CH:45]=[CH:44]1)=[O:42])[CH3:39]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 9982436N1-Ethyl-5-(2-(((4-(pyrrolidin-1-yl)piperidin-1-yl)carbonyl)amino)pyridin-4-yloxy)-1H-1-indolecarboxamideHCID 21949099Phenyl N-(4-(1-(ethylamino)carbonyl-1H-5-indolyl)oxy-2-pyridyl)carbamate

Product 1

HCID 10409125N1-Ethyl-5-(2-(piperidin-1-ylcarbonyl)amino-4-pyridyl)oxy-1H-1-indolecarboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N,N-Dimethylformamide (4 ml) and piperidine (0.31 ml, 3.13 mmol) were added to a mixture (0.336 g) of phenyl N-(4-(1-(ethylamino)carbonyl-1H-5-indolyl)oxy-2-pyridyl)carbamate and phenyl N-(4-(1-(ethylamino)carbonyl-1H-5-indolyl)oxy-2-pyridyl)-N-(phenoxycarbonyl)carbamate obtained in Example 77; 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 crystals (182 mg, 0.45 mmol).

Workup

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

Sources & evidence

ORD record
ord-ef5a9877989d4f60a673a60195e5509a
Source dataset
uspto-grants-2008_12
Patent number
US07468380B2

Reaction notes

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