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

HRID 2215537Notes

Reaction equation

HRID 2215537 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-fbf4d0ef11d94e5581ec6d4335b76592
Source dataset
uspto-grants-2006_09
Patent number
US07109219B2

Reaction notes

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