Carbamate → N4-(4-((1-(Ethylamino)carbonyl-1H-5-indolyl)oxy)-2-pyridyl)-4-morpholinecarboxamide

HRID 2376863Notes

Reaction equation

HRID 2376863 reaction equation
CN(C)C=O.[NH:6]1[CH2:11][CH2:10][O:9][CH2:8][CH2:7]1.C(=O)([O-])N.[CH2:16]([NH:18][C:19]([N:21]1[C:29]2[C:24](=[CH:25][C:26]([O:30][C:31]3[CH:36]=[CH:35][N:34]=[C:33]([NH:37][C:38](N4CCC(N5CCCC5)CC4)=[O:39])[CH:32]=3)=[CH:27][CH:28]=2)[CH:23]=[CH:22]1)=[O:20])[CH3:17]>C(OCC)C>[CH2:16]([NH:18][C:19]([N:21]1[C:29]2[C:24](=[CH:25][C:26]([O:30][C:31]3[CH:36]=[CH:35][N:34]=[C:33]([NH:37][C:38]([N:6]4[CH2:11][CH2:10][O:9][CH2:8][CH2:7]4)=[O:39])[CH:32]=3)=[CH:27][CH:28]=2)[CH:23]=[CH:22]1)=[O:20])[CH3:17]

Participants

6

Reactant 4

HCID 276CarbamateHCID 6228DimethylformamideHCID 8083MorpholineHCID 9982436N1-Ethyl-5-(2-(((4-(pyrrolidin-1-yl)piperidin-1-yl)carbonyl)amino)pyridin-4-yloxy)-1H-1-indolecarboxamide

Product 1

HCID 10092918N4-(4-((1-(Ethylamino)carbonyl-1H-5-indolyl)oxy)-2-pyridyl)-4-morpholinecarboxamide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

N,N-Dimethylformamide (5 ml) and morpholine (0.326 ml, 3.73 mmol) were added to a mixture (0.401 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; the organic layer was concentrated; and the obtained solid was washed with a solvent mixture of hexane:diethyl ether=1:1 to yield the title compound (255 mg, 0.62 mmol).

Workup

  1. customthe reaction mixture was partitioned between ethyl acetate and water
  2. concentrationthe organic layer was concentrated
  3. washand the obtained solid was washed with a solvent mixture of hexane

Sources & evidence

ORD record
ord-8e42e0d707ca4feea699858f7caac647
Source dataset
uspto-grants-2008_12
Patent number
US07468380B2

Reaction notes

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